Cesium fluoride → 2,4-Diamino-5-(2,4-dichlorophenyl)-6-fluoromethylpyrimidine

HRID 2292542Notes

Reaction equation

HRID 2292542 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([CH2:17]Br)[N:3]=1.[F-:19].[Cs+]>C1S(=O)(=O)CCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([CH2:17][F:19])[N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 19705067HCID 19705067, compound

Product 1

HCID 197050702,4-Diamino-5-(2,4-dichlorophenyl)-6-fluoromethylpyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,4-diamino-6-bromomethyl-5-(2,4-dichlorophenyl) pyrimidine (1.04 g) in tetramethylene sulphone (4.5 ml) was added cesium fluoride (1 g). The mixture was stirred and heated at 100° C. for 4 hours, cooled, diluted with water and extracted with chloroform. The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (silica; 19:1:0.1 dichloromethane/methanol/triethylamine) to give the title compound which was recrystallised from ethanol. 0.19 g, mp. 210°-211° C.

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (silica; 19:1:0.1 dichloromethane/methanol/triethylamine)

Sources & evidence

ORD record
ord-b5f94ec01ea9491c863cf7442a400a05
Source dataset
uspto-grants-1997_11
Patent number
US05684005

Reaction notes

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