4,6-Dichloro-5-nitropyrimidine → 4-Chloro-6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidine

반응식

[CH3:1][C:2]1([CH3:15])[O:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][O:3]1.[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21](Cl)[N:20]=[CH:19][N:18]=1.CC(N(C)C)=O>>[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([O:14][C:11]2[CH:12]=[CH:13][C:8]([CH:5]3[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][CH2:6]3)=[CH:9][CH:10]=2)[N:20]=[CH:19][N:18]=1

참가 물질

반응물 3

HCID 203124,6-Dichloro-5-nitropyrimidine

HCID 31374Dimethylacetamide

HCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenol

생성물 1

HCID 866651624-Chloro-6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidine수율 52.6%

실험 절차

To a solution of 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (500 mg, 0.0026 moles) and 4,6 dichloro-5-nitropyrimidine (600 mg, 0.0028 mole) in dimethyl acetamide (10 ml) K2CO3 (776 mg, 0.00577 mole) was added −20° C. The reaction mixture was stirred for about 2 hours at −10° C. to −18° C. The reaction mixture was then poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield crude product which was purified by column chromatography using 15% ethyl acetate in hexane as eluent to yield 500 mg product as pale yellow solid.