Triphenylphosphine → 9-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169296ノート

反応式

HRID 2169296 の反応式
O[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 178457437HCID 178457437、化合物

生成物 1

HCID 867259429-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione収率 43.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (258) (0.43 g, 0.85 mmol) and triphenyl phosphine (0.45 g, 1.71 mmol) in dry dichloromethane (10.0 mL) was added diethyl azidocarboxylate (0.34 mL, 2.13 mmol) at room temperature and the reaction stirred for 2 h. After completion of the reaction, the solvent was evaporated and the crude product was purified by normal silica gel column chromatography (using 2% methanol in dichloromethane) to get 9-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (259) (0.18 g, 43.0%) as a white solid.

後処理

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe crude product was purified by normal silica gel column chromatography (using 2% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-2dd4cb1e77414285b1b4c1348ae93ad8
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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