Potassium Carbonate → HCID 14306333, compound

HRID 622665Notes

Reaction equation

HRID 622665 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:18]1[S:22][CH:21]=[CH:20][C:19]=1CBr.CO.[CH2:27](Cl)Cl>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:27][C:18]2[S:22][CH:21]=[CH:20][CH:19]=2)=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5207033-(Bromomethyl)thiopheneHCID 53603492-Amino-6-chloropurineHCID 21226129Dichloromethane methanol

Product 1

HCID 14306333HCID 14306333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-chloropurine (Aldrich Chemical Co.) (7.47 g; 0.44 mol), potassium carbonate (6.64 g; 0.048 mol), and 3-thenylbromide (see U.S. Pat. No. 3,746,724) (7.8 g; 0.044 mol) in DMF (200 ml) was stirred under nitrogen at room temperature for 48 hours. The mixture was filtered and the filtrate evaporated to dryness under vacuum, ethyl ether was added and the precipitate was collected by filtration to give a mixture of 7- and 9-substituted chloropurines. A sample of pure 9 isomer was prepared by chromatography on silica gel with 5% methanol/methylene chloride as the eluting solvent to separate it from the 7-isomer. Analytical sample was obtained by crystallization from acetonemethanol mixture, yield 2.36 g, mp softens at 185° C. (dec) and then melts at 203°-204° C. (dec).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness under vacuum, ethyl ether
  3. additionwas added
  4. filtrationthe precipitate was collected by filtration
  5. customto give
  6. customto separate it from the 7-isomer
  7. customAnalytical sample was obtained by crystallization from acetonemethanol mixture, yield 2.36 g, mp

Sources & evidence

ORD record
ord-865ba8a7fc12421eabc8c25b96ac71dc
Source dataset
uspto-grants-1988_09
Patent number
US04772606

Reaction notes

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