Ammonia → Imidazo[1,5-a]pyrimidine-6-carboxamide,8-(3,3,4,4,4-pentafluorobutyl)-

HRID 2203389Notes

Reaction equation

HRID 2203389 reaction equation
[F:1][C:2]([F:23])([C:19]([F:22])([F:21])[F:20])[CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:14]([O:16]CC)=O)[N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12.[NH3:24]>>[F:1][C:2]([F:23])([C:19]([F:21])([F:22])[F:20])[CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:14]([NH2:24])=[O:16])[N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86679028Ethyl 8-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyrimidine-6-carboxylate

Product 1

HCID 76849900Imidazo[1,5-a]pyrimidine-6-carboxamide,8-(3,3,4,4,4-pentafluorobutyl)-

Procedure

A solution of the intermediate from Step D (0.3684 g, 1.092 mmol) and ammonia (11.70 mL, 82 mmol, 7 N in MeOH) was heated at 50° C. under N2 in a screw cap vial for 24 h. The reaction mixture was concentrated in vacuo to remove the excess amine to afford the desired product, as a yellow solid. m/z=309.1 (M+H).

Workup

  1. customcap vial for 24 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove the excess amine

Sources & evidence

ORD record
ord-5188009fae0646fc811dd728ebbb36f2
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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