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Ethyl Acetate → 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-(tetrahydro-pyran-4-yl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169371
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HRID 2169371 반응식
O[CH2:2][CH2:3][N:4]([CH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)[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:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[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.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(OCC)(=O)C>ClCCl.CCCCCC>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[C:5](=[O:6])[C:7]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519971HCID 178519971, 화합물

생성물 1

HCID 867260029-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-(tetrahydro-pyran-4-yl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione수율 60%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8058Hexane용매

실험 절차

5-Benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-(tetrahydro-pyran-4-yl)-amide (334) (90 mg, 0.16 mmol) and triphenylphosphine were taken up in dichloromethane (3 ml) at room temperature and diisopropyl azodicarboxylate was added slowly. Stirring was continued for 1 h while silica thin layer chromatography was performed (ethyl acetate:hexane=1:1, Rf=0.6). Dichloromethane (15 ml) was added to the reaction mixture, which was thereafter washed with water (10 ml) and brine (10 ml). The organic part was dried and concentrated under reduced pressure. The obtained residue was purified by nor mal silica gel (100-20 mesh) column chromatography using 30% ethyl acetate in hexane to get 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-(tetrahydro-pyran-4-yl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (335) (50 mg, 60%; 2 steps yield).

후처리

  1. washwas thereafter washed with water (10 ml) and brine (10 ml)
  2. customThe organic part was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by nor mal silica gel (100-20 mesh) column chromatography

출처 및 근거

ORD 기록
ord-9c078c3652ae45278cac5a2a9012d9f6
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045486B2

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