Formaldehyde → HCID 69059592, compound

HRID 1821590Notes

Reaction equation

HRID 1821590 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[N:14][C:15]=2[NH:17][CH2:18][C@@H:19]([OH:21])[CH3:20])[NH:10][N:9]=1.[CH2:31]=[O:32]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[N:14][C:15]=2[NH:17][CH2:18][CH:19]([OH:21])[CH3:20])[N:10]([CH2:31][OH:32])[N:9]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 178462355HCID 178462355, compound

Product 1

HCID 69059592HCID 69059592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-[3-(2-chlorophenyl)-6-(2,4-difluorophenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]propan-2-ol (2.4 g, 5.5 mmol) was suspended in 50 mL MeOH and stirred. Formaldehyde (3.3 mL, excess) was added and the reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 2.0 g of 1-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-hydroxymethyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol, MS (M+H)=462.

Workup

  1. stirringthe reaction mixture was stirred for 16 hours at room temperature
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21cec55d6f774955933dc62f6410104b
Source dataset
uspto-grants-2009_10
Patent number
US07608603B2

Reaction notes

Loading…