Sodium Carbonate → HCID 15136443, compound

HRID 2051206Notes

Reaction equation

HRID 2051206 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18].[N:19]1([NH2:24])[CH:23]=[CH:22][CH:21]=[CH:20]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH:24][N:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1365891-AminopyrroleHCID 10801475HCID 10801475, compound

Product 1

HCID 15136443HCID 15136443, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 6-chloro-9-(2-fluorobenzyl)-9H-purine (4.2 g, 16 mmole) and 1H-pyrrol-1-amine (3 g, 36 mmole) in 25 ml isopropanol was stirred at reflux for thirty minutes then was cooled, diluted with water, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride, was dried (anhydrous MgSO4), filtered and evaporated to 6 g of a solid. The solid was purified by flash chromatography (silica, 15% ethyl acetate in dichloromethane) to give 4.5 g of 9-(2-fluorobenzyl)-N-(1H-pyrrol-1-yl)-9H-purin-6-amine, m.p. 204°-206° C.

Workup

  1. temperatureat reflux for thirty minutes
  2. temperaturethen was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride
  6. dry with materialwas dried (anhydrous MgSO4)
  7. filtrationfiltered
  8. customevaporated to 6 g of a solid
  9. customThe solid was purified by flash chromatography (silica, 15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-b17b6efef657490e8685d9262f065697
Source dataset
uspto-grants-1991_05
Patent number
US05017578

Reaction notes

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