反应详情

温度

0 °C

Sodium hydride (60% dispersion in mineral oil 26 mg, 0.65 mmol) and acetamidoxime (48 mg, 0.65 mmol) were suspended in dry THF (4 ml) in an oven dried round bottom flask with stirring under nitrogen at 0° C. After 15 minutes stirring the ice bath was removed and the grey suspension refluxed 45 minutes to give a white suspension. 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (250 mg, 0.65 mmol) was added dissolved in dry THF (3 ml) and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue taken up in water (10 ml). The aqueous suspension was extracted exhaustively with chloroform and the organics dried over MgSO4. After evaporation the organic residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C. identified by 300 MHz nmr and ms m/z=408. Calculated: C 76.44, H 5.9, N 13.7; found: C 76.27, H 6.06, N 13.59.

1. customdried round bottom flask
2. stirringAfter 15 minutes stirring the ice bath
3. customwas removed
4. temperaturethe grey suspension refluxed 45 minutes
5. customto give a white suspension
6. temperaturereflux
7. customThe solvents were evaporated in vacuo
8. extractionThe aqueous suspension was extracted exhaustively with chloroform
9. dry with materialthe organics dried over MgSO4
10. customAfter evaporation the organic residue
11. customwas chromatographed (silica, chloroform/methanol, 9:1)
12. customto yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C.