Formaldehyde → HCID 178517689, compound

HRID 624802Notes

Reaction equation

HRID 624802 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:18][CH2:17]3)[N:12]3[N:19]=[CH:20][C:21](/[CH:22]=[C:23]4/[C:24](=[O:29])[NH:25][C:26](=[O:28])[NH:27]/4)=[C:11]3[N:10]=2)[CH:7]=1.[CH2:31]=[O:32]>C(#N)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:18][CH2:17]3)[N:12]3[N:19]=[CH:20][C:21](/[CH:22]=[C:23]4/[C:24](=[O:29])[N:25]([CH2:31][OH:32])[C:26](=[O:28])[NH:27]/4)=[C:11]3[N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 178518491HCID 178518491, compound

Product 1

HCID 178517689HCID 178517689, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To (Z)-5-((5-(5-chloro-2-fluorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (500 mg, 1.17 mmol) in acetonitrile (15 mL) and pyridine (1.5 mL) was added formaldehyde (37% aq) (5.0 mL). The reaction mixture was stirred at 65° C. for 5 minutes. Cooled to room temperature and filtered off the resulting solid. Washed with water and dried under vacuum to provide 450 mg (84%) of (Z)-5-((5-(5-chloro-2-fluorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-3-(hydroxymethyl)imidazolidine-2,4-dione as a yellow solid. LCMS (ES): >95% pure, m/z 458 [M+1]+.

Workup

  1. temperatureCooled to room temperature
  2. filtrationfiltered off the resulting solid
  3. washWashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0feb66c7aca24e7ebbabe0bb1fa82cba
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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