N,N-Dimethylaniline → 2,4-Diamino-5-(4-amino-3,5-dimethoxy-benzyl)-6-chloropyrimidine

HRID 462527

반응식

HRID 462527 반응식
CN(C)C1C=CC=CC=1.[NH2:10][C:11]1[N:16]=[C:15](O)[C:14]([CH2:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([NH2:27])=[C:21]([O:28][CH3:29])[CH:20]=2)=[C:13]([NH2:30])[N:12]=1.P(Cl)(Cl)([Cl:33])=O>>[NH2:10][C:11]1[N:12]=[C:13]([NH2:30])[C:14]([CH2:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([NH2:27])=[C:21]([O:28][CH3:29])[CH:20]=2)=[C:15]([Cl:33])[N:16]=1

참가 물질

4

반응물 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1784887982,6-diamino-5-[(4-amino-3,5-dimethoxyphenyl)methyl]-1H-pyrimidin-4-one

생성물 1

HCID 212809932,4-Diamino-5-(4-amino-3,5-dimethoxy-benzyl)-6-chloropyrimidine

실험 절차

2.5 G. of dimethylaniline were added dropwise to a suspension of 2.9 g. of 2,6-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-4-pyrimidinol in 15 ml. of phosphorus oxychloride with stirring. The mixture was brought to boil in 1 hour and then boiled under reflux for 4 hours. Thereafter, 8 to 9 ml. of phosphorus oxychloride were removed by distillation under reduced pressure and the residue was poured on to 80 g. of ice with stirring. The mixture was left to stand at room temperature for 6 days and then 35 ml. of concentrated ammonia were added portionwise. After standing for 2 hours, the solid material was removed by filtration under vacuum, dried, recrystallized from dimethylformamide/ether, whereby there was obtained 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-6-chloro-pyrimidine having a melting point of 222°-224° C.

후처리

  1. temperatureunder reflux for 4 hours
  2. customof phosphorus oxychloride were removed by distillation under reduced pressure
  3. additionthe residue was poured on to 80 g
  4. waitThe mixture was left
  5. waitto stand at room temperature for 6 days
  6. additionof concentrated ammonia were added portionwise
  7. waitAfter standing for 2 hours
  8. customthe solid material was removed by filtration under vacuum
  9. customdried
  10. customrecrystallized from dimethylformamide/ether

출처 및 근거

ORD 기록
ord-06bec8bc0354453793001f8168999c61
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04515948

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