Ammonia methanol → HCID 89580070, compound

HRID 2276811Notes

Reaction equation

HRID 2276811 reaction equation
[NH3:1].CO.[C:4]([C:6]1[CH:30]=[CH:29][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:22]=[C:21]([C:23]([O:25]C)=O)[CH:20]=[C:19]([CH:27]=[CH2:28])[N:18]=3)=[CH:13][CH:12]=2)=[CH:8][C:7]=1[C:31]([F:34])([F:33])[F:32])#[N:5]>CO>[C:4]([C:6]1[CH:30]=[CH:29][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[N:22]=[C:21]([C:23]([NH2:1])=[O:25])[CH:20]=[C:19]([CH:27]=[CH2:28])[N:18]=3)=[CH:15][CH:16]=2)=[CH:8][C:7]=1[C:31]([F:33])([F:34])[F:32])#[N:5]

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 89579960HCID 89579960, compound

Product 1

HCID 89580070HCID 89580070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50-mL vial with a screw-top septum, methyl 2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-vinylpyrimidine-4-carboxylate was dissolved in MeOH (2 mL) and stirred at room temperature. To the solution was added 7N NH3/MeOH (5 mL) and the reaction mixture was stirred for 20 hours. The reaction mixture was concentrated under reduced pressure and purified using Combiflash with a gradient of methanol (30% max) in chloroform to provide 2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-vinylpyrimidine-4-carboxamide (270 mg) as a white solid. LC/MS: m/z=411 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred for 20 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-59d1c8d0ff334c548eb075821b5cb703
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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