HCID 20195974, compound → HCID 178503460, compound

HRID 653188Notes

Reaction equation

HRID 653188 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1.Cl.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][N:13]=1>Cl.C(Cl)Cl.CO>[OH:9][C:7]1[C:6]([CH:18]([C:15]2[CH:14]=[N:13][C:12]([CH3:11])=[CH:17][CH:16]=2)[OH:19])=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

5

Reactant 2

HCID 20195974HCID 20195974, compoundHCID 178503462HCID 178503462, compound

Product 1

HCID 178503460HCID 178503460, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 10.0 g (0.07 mol) of 2-methylthio-4-hydroxypyrimidine and 12.4 g (0.079 mol) of 2-methyl-5-formylpyridine hydrochloride in 75 ml of concentrated hydrochloric acid was heated at reflux for 1 hour. After working up as in Example 1 an oil is obtained which is taken up in methylene chloride-methanol then recrystallized from ethyl acetate to give 4-hydroxy-5-[(6-methyl-3-pyridinyl)hydroxymethyl]-2-methylthiopyrimidine; 9.3 g (50%), m.p. 140°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customis obtained which
  4. customthen recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-93ebfa4f36bd4ceab8f7d1d3cd70cb16
Source dataset
uspto-grants-1987_06
Patent number
US04675406

Reaction notes

Loading…