Hydrochloric Acid → 6-chloro-9-methyl-9H-purine

HRID 345420Notes

Reaction equation

HRID 345420 reaction equation
[NH2:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[N:6][C:7]=1[NH:8][CH3:9].Cl.[CH:12](OCC)(OCC)OCC>>[Cl:10][C:3]1[N:4]=[CH:5][N:6]=[C:7]2[C:2]=1[N:1]=[CH:9][N:8]2[CH3:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 3084776-chloro-N4-methylpyrimidine-4,5-diamine

Product 1

HCID 948446-chloro-9-methyl-9H-purine

Procedure

To 5.0 g (31 mmol) of 5-amino-4-chloro-6-methylaminopyrimidine suspended in 200 ml of triethyl orthoformate was added 2.6 ml of concentrated HCl and the resultant mixture stirred overnight at room temperature (r.t.). The white precipitate was then collected, washed with ether which was then combined with the orthoformate which was concentrated to give pure 6-chloro-9-methylpurine by tlc (thin layer chromatography) (silica, 90:10 CHCl3 :CH3OH). The filtered solid was returned to 150 ml ethyl orthoformate, treated with 1.0 ml concentrated HCl and stirred at 60° C. for 18 hours. The solution was evaporated and the solids combined to give 5 g (94%) of 6-chloro-9-methylpurine, m.p. 205°-207° C.

Workup

  1. customThe white precipitate was then collected
  2. washwashed with ether which
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-41e82bbf0c404684b525a0c95ae379c2
Source dataset
uspto-grants-1991_10
Patent number
US05057517

Reaction notes

Loading…