Pyrimidine, 2-ethenyl- (9CI) synthesis
- Product Name:Pyrimidine, 2-ethenyl- (9CI)
- CAS Number:51394-43-5
- Molecular formula:C6H6N2
- Molecular Weight:106.13
Yield:51394-43-5 71%
Reaction Conditions:
Stage #1: triphenyl(pyrimidin-2-ylmethyl)phosphonium chloridewith sodium t-butanolate in tetrahydrofuran at 20; for 2 h;
Stage #2: formaldehyd in tetrahydrofuran;water; for 18 h;
Steps:
14.A
Sodium tert-butoxide (1.22 g, 12.7 mmol) was added to a solution of C64 (4.5 g, 12.7 mmol) in THF (13 mL), and the reaction mixture was stirred at room temperature for 2 h. A solution of formaldehyde in water (37%, 2.8 mL, 38 mmol) was added and the mixture was stirred for an additional 18 h. The reaction mixture was pre-adsorbed on silica gel and purified twice by chromatography (Eluant: diethyl ether) to afford C67. Yield: 950 mg, 8.96 mmol, 71%. 1H NMR (400 MHz, CDCl3) δ 5.72 (dd, J=10.6, 2.1 Hz, 1H), 6.60 (dd, J=17.4, 2.1 Hz, 1H), 6.86 (dd, J=17.4, 10.6 Hz, 1H), 7.11 (t, J=4.9 Hz, 1H), 8.68 (d, J=4.8 Hz, 2H).
References:
US2010/190771,2010,A1 Location in patent:Page/Page column 34-35
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