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1,4,5,6-Tetrahydropyrimidin-2-amine → (2S)-2-benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic acid tert-butyl ester

HRID 854248
ノート
印刷プレビュー

反応式

HRID 854248 の反応式
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH:17][CH2:18][C@H:19]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])C.[NH:39]1[CH2:44][CH2:43][CH2:42][N:41]=[C:40]1[NH2:45]>CN(C)C=O>[C:23]([O:22][C:20](=[O:21])[C@@H:19]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:18][NH:17][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[C:14]=1[N:15]=[CH:16][N:8]2[CH2:7][CH2:6][CH2:5][C:4](=[O:3])[NH:45][C:40]1[NH:41][CH2:42][CH2:43][CH2:44][N:39]=1)([CH3:26])([CH3:24])[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 155472654-[6-((2S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-purin-9-yl]-butyric acid ethyl ester

生成物 1

HCID 15547266(2S)-2-benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

200 mg (0.38 mmol) of 4-[6-((2S)-2-benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-purin-9-yl]-butyric acid ethyl ester was dissolved in 2 ml of dimethylformamide and 188 mg (1.9 mmol) of 1,4,5,6-tetrahydro-pyrimidin-2-ylamine was added. The solution was stirred at room temperature for 16 hours. The solvent was removed in vacuo, the residue was dissolved in dichloromethane and the solution was washed twice with 10% aqueous citric acid solution and twice with water. Product in the combined aqueous phase was extracted five times with dichloromethane. The combined organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane/methanol (10/1), followed by DCM/AcOH/water (85:15:1.5:1.5). Yield: 70.6 mg.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washthe solution was washed twice with 10% aqueous citric acid solution and twice with water
  4. extractionProduct in the combined aqueous phase was extracted five times with dichloromethane
  5. dry with materialThe combined organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol (10/1)

出典と根拠

ORDレコード
ord-e8d6a6406aee412594ac30ea19a7d3fd
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259159B2

反応ノート

読み込み中…

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