Chlorodifluoromethane → 4-(Difluoromethoxy)-6-methylpyrimidin-2-amine

HRID 1633341Notes

Reaction equation

HRID 1633341 reaction equation
[F:1][CH:2]([F:4])Cl.[NH2:5][C:6]1[N:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:13])[N:7]=1>O.[OH-].[Na+].O1CCOCC1>[NH2:5][C:6]1[N:11]=[C:10]([O:12][CH:2]([F:4])[F:1])[CH:9]=[C:8]([CH3:13])[N:7]=1

Participants

6

Reactant 2

HCID 6372ChlorodifluoromethaneHCID 178429408HCID 178429408, compound

Product 1

HCID 28173904-(Difluoromethoxy)-6-methylpyrimidin-2-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Gaseous difluorochloromethane is introduced, over a period of 12 hours at a temperature of 70° to 75° C., into a solution of 62.5 g of 2-amino-4-hydroxy-6-methyl-pyrimidine in 500 ml of water, 100 ml of 40% sodium hydroxide solution and 100 ml of dioxane. There are added during this time, in each case at intervals of 1 hour and in equal portions, a total of 160 g of solid sodium hydroxide. The organic phase is separated, and concentrated to about 1/10 of its volume; the residue is poured into water, and the solid substance which has precipitated is removed. The yield is 39.9 g of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine, m.p. 136° to 137° C. (compound No. 1.1).

Workup

  1. additionThere are added during this time, in each case at intervals of 1 hour and in equal portions
  2. customThe organic phase is separated
  3. concentrationconcentrated to about 1/10 of its volume
  4. additionthe residue is poured into water
  5. customthe solid substance which has precipitated
  6. customis removed

Sources & evidence

ORD record
ord-24850676f08d42bda35986036e92133e
Source dataset
uspto-grants-1984_10
Patent number
US04480101

Reaction notes

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