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Methanol → 2-Methyl-6-[1-[1-[bis(4-fluorophenyl)methyl]piperazin-4-yl]-2-hydroxy-3-propanylthio]purine

HRID 373631
ノート
印刷プレビュー

反応式

HRID 373631 の反応式
[H-].[Na+].[CH3:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([SH:13])[N:5]=1.Cl[CH2:15][CH:16]([OH:39])[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH:24]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1.CO>CN(C=O)C.C(Cl)Cl>[CH3:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([S:13][CH2:15][CH:16]([OH:39])[CH2:17][N:18]2[CH2:19][CH2:20][N:21]([CH:24]([C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)[C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH2:22][CH2:23]2)[N:5]=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 24758Sodium hydrideHCID 103851541-(1-Chloro-2-hydroxy-3-propanyl)-4-(4,4'-difluorobenzhydryl)piperazineHCID 178433540HCID 178433540、化合物

生成物 1

HCID 104814462-Methyl-6-[1-[1-[bis(4-fluorophenyl)methyl]piperazin-4-yl]-2-hydroxy-3-propanylthio]purine収率 23.7%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
3 回
HCID 6344Dichloromethane溶媒

実験手順

To NaH (2.4 mmol, 115 mg, 50% in oil, pentane washed and decanted), in DMF (5 mL) was added 2-methyl-6-mercaptopurine (400 mg, 2.4 mmol) in portions, at 0° After stirring 2 h 1-(1-chloro-2-hydroxy-3-propanyl)-4-(4,4'- difluorobenzhydryl)piperazine (2.4 mmol, 0.914 g) was added in DMF (5 mL) dropwise over 15 min, at 0° C., under nitrogen. After three days, the solution was filtered and the DMF removed from the filtrate in vacuo (vacuum oven, 1 mm Hg, 60° C.) to give the crude product. Silica gel flash column chromatography using 10% MeOH:CH2Cl2 gave the product with DMF. This product was dried 72 h in vacuo (room temperature, 1 mm Hg) to give pure product (290 mg, 23.2%). mp 83°-86° C. (dec.) DCI/MS (M+1)=511. (300 MHz) 1H NMR (CDCl3)δ: 8.1 (s, 1H), 7.3 (m, 4H), 6.95 (m, 4H), 4.2 (s, 1H), 4.15 (m, 1H), 3.4 and 3.6 (d of d, 2H), 2.65 (s, 3H), 2.6 (M, 6H), 2.4 (m, 4H).

後処理

  1. filtrationthe solution was filtered
  2. customthe DMF removed from the filtrate in vacuo (vacuum oven, 1 mm Hg, 60° C.)
  3. customto give the crude product
  4. customThis product was dried 72 h in vacuo (room temperature, 1 mm Hg)

出典と根拠

ORDレコード
ord-7643864118dc4f50a55a9aa707f90283
出典データセット
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05164390

反応ノート

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