Hydrochloric Acid → Aditeren

HRID 1589247Notes

Reaction equation

HRID 1589247 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9]O)=[CH:4][N:3]=1.NC1N=C(N)C(C#N)=CN=1.[CH3:21][O:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:24]=1[NH2:25].Cl>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:28]2[CH:27]=[C:26]([O:30][CH3:31])[C:24]([NH2:25])=[C:23]([O:22][CH3:21])[CH:29]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 95940Benzenamine, 2,6-dimethoxy-HCID 2821152,4-Diaminopyrimidine-5-carbonitrileHCID 2958782,4-Diamino-5-pyrimidinemethanol

Product 1

HCID 176875AditerenYield 86.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,4-diamino-5-hydroxymethylpyrimidine (4.30 g, 30.0 mmol), prepared from 2,4-diamino-5-cyanopyrimidine as described in U.K. Pat. No. 1 413 472, 2,6-dimethoxyaniline (5.05 g, 33.0 mmol), acetic acid (60 mL), and concentrated hydrochloric acid (4.2 mL) was refluxed for 41/2 hours, cooled, and filtered to give the hydrochloride salt of the title compound (7.13 g, 76.2%). The salt was dissolved in water and the solution made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered, washed with water, and dried to give the title compound (5.18 g, 62.7%).

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-ee60d8fc91e14d57a05c49a77102e768
Source dataset
uspto-grants-1986_02
Patent number
US04568744

Reaction notes

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