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Chapter 2 Synthesis of substituted pyrimidines via Wittig Table 1: Optimization of reaction condition for synthesis of Aw-01 using variety of bases and solvents. Entry Base Solvents Yield Time hrs. 1 NaH 2 PO 4 DMSO 65 7.0 2 NaH 2 PO 4 THF 70 7.5 3 NaH 2 PO 4 water 76 5.0 4 Na 2 HPO 4 DMSO 68 6.5 5 Na 2 HPO 4 THF 77 6.0 6 Na 2 HPO 4 water 80 4.5 7 Na 5 P 3 O 10 DMSO 85 7.0 8 Na 5 P 3 O 10 THF 83 5.0 9 Na 5 P 3 O 10 water 90 3.0 The structure of INT-01 was established on the basis of their elemental analysis and spectral data (MS, IR, 1 HNMR, and 13 C NMR). The analytical data for INT-01 revealed a molecular formula C 14 H 14 ClFN 2 O (m/z 280). The 1 H NMR spectrum revealed doublet at δ = 1.30-1.33 ppm assigned to isopropyl-CH 3 , a singlet at δ = 2.09 ppm assigned to the –OH protons, a multiplet at δ = 3.67-3.69 ppm assigned to the isopropyl -CH protons, a singlet at δ = 4.69 ppm assigned to the –CH 2 protons, two triplet at δ = 7.28-7.34 ppm and 7.88-7.92 assigned to the aromatic protons. The structure of INT-02 was established on the basis of their elemental analysis and spectral data (MS, IR, 1 H NMR, and 13 C NMR). Structure INT-02 was supported by its mass (m/z 605), which agrees with its molecular formula C 32 H 28 BrClFN 2 P , its 1 H NMR spectrum had signals at δ = 0.90 (s, 6H, 2 x i prCH 3 ), 2.99-3.03 (m, 1H, i prCH), 5.67 (s, 2H, CH 2 ), 6.97-7.02 (t, 2H, Ar-H), 7.26-7.33 (m, 8H, Ar-H), 7.57 (s, 6H, Ar-H), 7.75-7.80 (m, 3H, Ar-H). Reaction of pyrimidine phosphorous ylide (INT-02) with various benzaldehydes using Sodium tripolyphosphate as base in aqueous media to afford highly (E)-selective product AW-01 to AW-20 in moderate to excellent yield. Require reaction time and obtained (%) of yield summarized in Table-2. Department of Chemistry, <strong>Saurashtra</strong> university, Rajkot-360005 58
Chapter 2 Synthesis of substituted pyrimidines via Wittig Table-2: Synthesis of substituted pyrimidines via Wittig reaction using sodium tripolyphosphate under aqueous media. Entry R Yield (%) Time hrs AW-01 C 6 H 4 90 3.0 AW-02 4-NO 2 C 6 H 4 92 2.5 AW-03 4-ClC 6 H 4 84 3.0 AW-04 C 5 H 4 S 89 3.5 AW-05 C 5 H 4 O 90 4.0 AW-06 C 8 H 7 N 82 3.5 AW-07 2-NO 2 C 6 H 4 79 3.0 AW-08 4-ClC 6 H 4 85 3.5 AW-09 3-0CH 3 ,4-OHC 6 H 4 93 3.5 AW-10 3,4-di-OCH 3 C 6 H 3 95 3.0 AW-11 4-N(CH 3 ) 2 C 6 H 4 82 3.0 AW-12 4-FC 6 H 4 83 3.5 AW-13 3-NO 2 C 6 H 4 94 4.0 AW-14 4-BrC 6 H 4 90 4.5 AW-15 2-OHC 6 H 4 88 3.0 AW-16 4-OCH 3 C 6 H 4 76 3.5 AW-17 2,5-di-OCH 3 C 6 H 3 89 3.0 AW-18 3-BrC 6 H 4 83 4.0 AW-19 4-ClC 6 H 4 81 3.0 AW-20 3-OHC 6 H 4 77 4.0 The structure of AW-01 to AW-20 was established on the basis of their elemental analysis, spectral data (MS, IR, 1 H NMR, and 13 C NMR) and (E)-selectivity of products was supported by NMR spectrum. Structure of AW-02 was supported by its mass (m/z 398), which agrees with its molecular formula C 21 H 17 ClFN 3 O 2, its 1 H NMR spectrum had signals at δ = 1.34-1.36 (d, 6H, 2 x i prCH 3 ), 3.44-3.49 (m, 1H, i prCH), 6.55-6.61 (d, 1H, j=16.5Hz, ethylene-H), 7.08-7.17 (m, 3H, Ar-H & ethylene- H), 7.48-7.51 (d, 2H, j=20.4Hz, Ar-H), 7.64-7.68 (t, 2H, Ar-H), 8.19-8.22 (d, 2H, j=8.4Hz, Ar-H). Department of Chemistry, <strong>Saurashtra</strong> university, Rajkot-360005 59
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Saurashtra University Re - Accredit
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Statement under O.Ph.D.7 of Saurash
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I am thankful to FIST/DST and SAP/U
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Chapter 4 Synthesis and Characteriz
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Chapter - 1 Palladium Catalyzed Syn
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Chapter 1 Synthesis of functionaliz
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Chapter 3 Synthesis of trisubstitut
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Chapter 6 Synthesis of benzodiazepi
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pyrazole derivative were faster and
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Conferences participated 1. “15 t
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