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Methanol → 9-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169438
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HRID 2169438 반응식
O[CH2:2][CH2:3][N:4]([CH3:37])[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([N:28]3[C:32]4=[N:33][CH:34]=[CH:35][CH:36]=[C:31]4[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.CO>ClCCl.C(OCC)(=O)C>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([N:28]3[C:32]4=[N:33][CH:34]=[CH:35][CH:36]=[C:31]4[CH:30]=[CH:29]3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:2][CH2:3][N:4]([CH3:37])[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 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178484643HCID 178484643, 화합물

생성물 1

HCID 867260709-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione수율 30%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (406) (210 mg, 0.42 mmol) in dichloromethane (30 mL) was added triphenyl phosphine (550 mg, 2.09 mmol) followed by diisopropyl azodicarboxylate (0.2 mL, 1.26 mmol) at room temperature and stirring was continued for 10 min (TLC, 5% methanol in ethyl acetate, Rf=0.2). The reaction mixture was concentrated under reduced pressure to get a crude product, which was purified by Prep-TLC plate (mobile phase 5% methanol in ethyl acetate) to get 9-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (407) (60 mg, 30%) as a white solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get a crude product, which
  3. customwas purified by Prep-TLC plate (mobile phase 5% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-17ba63bcfd4743438559f47e44718f36
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045486B2

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