Diisopropylethylamine → 5-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-

HRID 1435167노트

반응식

HRID 1435167 반응식
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([S:11][CH2:12][CH3:13])[N:3]=1.F[P-](F)(F)(F)(F)F.[N:21]1([O:30][C:31](N(C)C)=[N+](C)C)[C:25]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:31][O:30][N:21]([CH3:25])[C:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([S:11][CH2:12][CH3:13])=[N:5][CH:6]=1)=[O:10]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 2753004-Amino-2-(ethylthio)pyrimidine-5-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-수율 98%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid (1.00 g, 5.40 mmol, Sigma) in dimethylformamide were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.06 g, 8.1 mmol, Aldrich), 1-hydroxy-benzotriazole hydrate (1.09 g, 8.1 mmol, Aldrich) followed by diisopropylethylamine (3.94 g, 29.7 mmol) at 0° C. After stirring for 10-15 minutes, N,O-dimethyl-hydroxylamine. HCl (790 mg, 8.1 mmol, Aldrich) was added. The reaction was stirred at 0° C. to room temperature for 2 hours and then diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated. The crude product was purified on silica gel with 1:1 hexane/ethyl acetate to give 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methyl-amide as a white solid (1.189 g, 98% yield). HRMS, observed: 242.0836; Calcd for M+: 242.0837

후처리

  1. stirringThe reaction was stirred at 0° C. to room temperature for 2 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified on silica gel with 1:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-96054699ef8541609acd2f8fe39a5820
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615634B2

반응 노트

불러오는 중…