Ammonia → HCID 11464606, compound

HRID 2105206Notes

Reaction equation

HRID 2105206 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)=O.[NH3:34].CO>>[C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)(=[O:2])[NH2:34]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 113053826-Methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

Product 1

HCID 11464606HCID 11464606, compoundYield 93%

Procedure

A mixture of 6-methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 56) (200 mg, 0.45 mmol) and a solution of 7N ammonia in methanol (7 ml, 49 mmol) was heated at 65° C. in a sealed vessel under microwave irradiation for 1 hour. The reaction mixture was evaporated, dissolved in methanol and passed through a 50 g isolute SCX-2 ion exchange column. The column was eluted with methanol to elute any neutrals, followed by 7M methanolic ammonia to elute the product. The solvent was removed by evaporation and the residue triturated with diethylether. The resulting solid was collected by filtration to give the title compound (180.0 mg, 93%).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in methanol
  3. washThe column was eluted with methanol
  4. washto elute any neutrals
  5. washto elute the product
  6. customThe solvent was removed by evaporation
  7. customthe residue triturated with diethylether
  8. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-0566f0426aad45928672ea7be60a9d89
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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