Ammonia → HCID 21070552, compound

HRID 1435327Notes

Reaction equation

HRID 1435327 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([C:11]2[C:19]3[O:18][CH:17]=[CH:16][C:15]=3[CH:14]=[C:13]([F:20])[CH:12]=2)=[O:10])=[CH:4][N:3]=1.[NH3:21]>C1(C)C=CC=CC=1>[NH2:21][C:6]1[C:5]([C:9]([C:11]2[C:19]3[O:18][CH:17]=[CH:16][C:15]=3[CH:14]=[C:13]([F:20])[CH:12]=2)=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21070509HCID 21070509, compound

Product 1

HCID 21070552HCID 21070552, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At 20° C., a stirred suspension of (2,4-dichloro-pyrimidin-5-yl)-(5-fluoro-benzofuran-7-yl)-methanone (0.80 g, 2.6 mmol, Step E) in toluene (70 mL) was treated with a slow stream of ammonia gas (Matheson) for 1 hour. The suspension was cooled, filtered and the filter cake washed with water. The filter cake was dissolved in acetonitrile, filtered through celite and the solvent removed to give a solid. This was crystallized from acetonitrile to give 0.4 g of (4-amino-2-chloro-pyrimidin-5-yl)-(5-fluoro-benzofuran-7-yl)-methanone (52%) as a white solid. HRMS, observed: 291.0208; Calcd for (M+H)+: 291.0211

Workup

  1. temperatureThe suspension was cooled
  2. filtrationfiltered
  3. washthe filter cake washed with water
  4. dissolutionThe filter cake was dissolved in acetonitrile
  5. filtrationfiltered through celite
  6. customthe solvent removed
  7. customto give a solid
  8. customThis was crystallized from acetonitrile

Sources & evidence

ORD record
ord-b7fdd21261284b9f919a269957f8d04a
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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