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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
ノート
印刷プレビュー

反応式

HRID 2169438 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178484643HCID 178484643、化合物

生成物 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-dione収率 30%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-17ba63bcfd4743438559f47e44718f36
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09045486B2

反応ノート

読み込み中…

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