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

HRID 373631
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HRID 373631 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 103851541-(1-Chloro-2-hydroxy-3-propanyl)-4-(4,4'-difluorobenzhydryl)piperazineHCID 178433540HCID 178433540, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
3회
HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7643864118dc4f50a55a9aa707f90283
출처 데이터셋
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05164390

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