Methanol → 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169367노트

반응식

HRID 2169367 반응식
[CH:1]1([CH2:4][N:5]([CH2:36][CH2:37]O)[C:6]([C:8]2[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]3([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:28][CH2:27][CH2:26][CH2:25]3)[N:9]=2)=[O:7])[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.CO>ClCCl.C(OCC)(=O)C>[CH2:15]([O:14][C:13]1[C:12](=[O:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)[N:9]2[CH2:37][CH2:36][N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6](=[O:7])[C:8]=12)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519972HCID 178519972, 화합물

생성물 1

HCID 867259989-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione수율 74%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (330) (390 mg, 0.73 mmol) in dichloromethane (30 mL) was added triphenyl phosphine (286 mg, 1.09 mmol) and diisopropyl azodicarboxylate (0.22 mL, 1.09 mmol) at room temperature the reaction was stirred for 30 minutes (TLC; 5% methanol in ethyl acetate/UV/SiO2, Rf=0.05). The dichloromethane was removed in vacuo and the crude mass was purified by silica gel (normal, 100-200 mesh) column chromatography using gradient eluent of 1% to 5% methanol in dichloromethane to get pure 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (331) (280 mg, 74%) as a white sticky solid.

후처리

  1. customThe dichloromethane was removed in vacuo
  2. customthe crude mass was purified by silica gel (normal, 100-200 mesh) column chromatography

출처 및 근거

ORD 기록
ord-b2944dff281642f7ba150799bf8ecc06
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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