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

HRID 1435167ノート

反応式

HRID 1435167 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-96054699ef8541609acd2f8fe39a5820
出典データセット
uspto-grants-2009_11
特許番号
US07615634B2

反応ノート

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