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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, Saurashtra university, Rajkot-360005 58