Ammonia → HCID 21996901, compound

HRID 1197410Notes

Reaction equation

HRID 1197410 reaction equation
[NH3:1].F[C:3]1[N:8]=[C:7]([F:9])[C:6]([O:10][CH:11]([F:13])[F:12])=[C:5]([Cl:14])[N:4]=1>O1CCCC1>[NH2:1][C:3]1[N:4]=[C:5]([Cl:14])[C:6]([O:10][CH:11]([F:13])[F:12])=[C:7]([F:9])[N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21996893HCID 21996893, compound

Product 1

HCID 21996901HCID 21996901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

At -75° to -70° C. and over a period of 1 hour, 9.8 g (0.578 mol) of gaseous ammonia was gassed while stirring into a mixture of 62.5 g (0.289 mol) of 2,4-difluoro-6-chlorodifluoromethoxypyrimidine in 300 ml of tetrahydrofuran. The mixture was stirred for 1 hour at -70° C. and then heated to room temperature. The precipitate was suction filtered, partitioned between ethyl acetate and water, and the organic phase was dried over magnesium sulfate. The reaction filtrate was evaporated down, dissolved in the abovementioned ethyl acetate phase, chromatographed over silica gel (5:1 ligroin/ether mixture) and evaporated down. There was obtained 46.5 g (75.3% of theory) of the title compound as colorless crystals of melting point 77°-80° C.

Workup

  1. temperatureheated to room temperature
  2. filtrationfiltered
  3. custompartitioned between ethyl acetate and water
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customThe reaction filtrate was evaporated down
  6. dissolutiondissolved in the abovementioned ethyl acetate phase
  7. customchromatographed over silica gel (5:1 ligroin/ether mixture)
  8. customevaporated down

Sources & evidence

ORD record
ord-0bf115b0ee35471393969b67a3b1da9d
Source dataset
uspto-grants-1994_01
Patent number
US05276007

Reaction notes

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