Hydrochloride methanol → 1,4,5,6-Tetrahydro-N-methoxy-5-pyrimidinamine dihydrochloride

HRID 129821Notes

Reaction equation

HRID 129821 reaction equation
[ClH:1].[CH3:2][O:3][N:4]=[C:5]1[CH2:10][NH:9][CH:8]=[N:7][CH2:6]1.Cl.CO.[BH4-].CN(C)C>CO>[ClH:1].[ClH:1].[CH3:2][O:3][NH:4][CH:5]1[CH2:10][NH:9][CH:8]=[N:7][CH2:6]1

Participants

5

Reactant 3

HCID 21893726Hydrochloride methanolHCID 736056051,6-Dihydro-5(4H)-pyrimidinone O-methyloxime monohydrochlorideHCID 131719211Trimethylamine borohydride

Product 1

HCID 193704701,4,5,6-Tetrahydro-N-methoxy-5-pyrimidinamine dihydrochlorideYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,6-dihydro-5-(4H)-pyrimidinone O-methyloxim monohydrochloride (2.8 g, 17.1 mmol) in dry methanol was added dropwise to a stirred solution of HCl/methanol (49 ml of a 3N solution) and trimethylamine borohydride (1.36 g, 18.7 mmol) at room temperature under a nitrogen atmosphere. After 1 hour the reaction product crystallised spontaneously. Recrystallization from methanol/ethyl acetate gave a light-brown material in 38% yield (1.30 g). Mp. 214.0° C.

Workup

  1. customAfter 1 hour the reaction product crystallised spontaneously
  2. customRecrystallization from methanol/ethyl acetate
  3. customgave a light-brown material in 38% yield (1.30 g)

Sources & evidence

ORD record
ord-5d150106284f449cb8c5312a003774d5
Source dataset
uspto-grants-1995_11
Patent number
US05470856

Reaction notes

Loading…