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

HRID 373631
Notes
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Reaction equation

HRID 373631 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolvent3×HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7643864118dc4f50a55a9aa707f90283
Source dataset
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05164390

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes