2-Chloropyrimidine → HCID 19785323, compound

HRID 256671Notes

Reaction equation

HRID 256671 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[N:19]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:20]3[C:25]([N:26]=2)=[CH:24][N:23]=[CH:22][N:21]=3)[CH2:13][CH2:12]1.C(=O)([O-])O.[Na+]>C(O)C>[F:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:19]2[C:18]([NH:17][CH:14]3[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][NH:8][C:2]4[N:7]=[CH:6][CH:5]=[CH:4][N:3]=4)[CH2:16][CH2:15]3)=[N:26][C:25]3[C:20]2=[N:21][CH:22]=[N:23][CH:24]=3)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 19785318N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine

Product 1

HCID 19785323HCID 19785323, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.7 parts of 2-chloropyrimidine, 5.5 parts of N-[1-(2 aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine, 1.5 parts of sodium hydrogen carbonate and 160 parts of ethanol was stirred and refluxed for 20 hours. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 4.5 parts (67%) of 9-[(4-fluorophenyl)methyl]-N-[1-[2-(2-pyrimidinylamino)ethyl]-4-piperidinyl]-9H-purin-8-amine; mp. 164.1° C. (compound 164).

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-547c46afb598489a92369f1f60ef5336
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

Loading…