HCID 13961960, compound → HCID 178503558, compound

HRID 2309106Notes

Reaction equation

HRID 2309106 reaction equation
N([O-])=[O:2].[Na+].Cl[C:6]1[CH:11]=[C:10]([O:12][CH:13]([F:15])[F:14])[N:9]=[C:8]([S:16][CH3:17])[N:7]=1>CN(C)C=O>[F:14][CH:13]([F:15])[O:12][C:10]1[CH:11]=[C:6]([OH:2])[N:7]=[C:8]([S:16][CH3:17])[N:9]=1

Participants

4

Reactant 2

HCID 13961960HCID 13961960, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 178503558HCID 178503558, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Over 50 minutes, a solution of 8.8 g (0.127 mole) of sodium nitrite in 10 ml of dimethylformamide is added dropwise at 140° C. to a solution of 8.7 g (0.038 mole) of 4-chloro-6-difluoromethoxy-2-methylthiopyrimidine in 10 ml of dimethylformamide. When the addition of the sodium nitrite is complete, the mixture is stirred for 2 hours at 140° to 150° C. The solvent is then evaporated off in vacuo and the residue is crystallised from 1N hydrochloric acid, affording 5.6 g (70% of theory) of 4-difluoromethoxy-6-hydroxy-2-methylthiopyrimidine with a melting point of 236°-237° C.

Workup

  1. customThe solvent is then evaporated off in vacuo
  2. customthe residue is crystallised from 1N hydrochloric acid

Sources & evidence

ORD record
ord-d2b6cc7673524f8a89b8382c16ec5160
Source dataset
uspto-grants-1987_09
Patent number
US04692524

Reaction notes

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