Ammonia → HCID 21070552, compound

HRID 1371748Notes

Reaction equation

HRID 1371748 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-58a0ffdc578a4a8a8d3fda352cb8fdfe
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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