HCID 21939176, compound → HCID 178432483, compound

HRID 1896191Notes

Reaction equation

HRID 1896191 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[N:3]=1.[F:17][C:18]1[CH:19]=[C:20]2[C:26]([NH2:27])=[N:25][NH:24][C:21]2=[N:22][CH:23]=1>CN1C(=O)CCC1>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:4]1[N:3]=[C:2]([NH:27][C:26]2[C:20]3[C:21](=[N:22][CH:23]=[C:18]([F:17])[CH:19]=3)[NH:24][N:25]=2)[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=1

Participants

4

Reactant 2

HCID 21939176HCID 21939176, compoundHCID 178509230HCID 178509230, compound

Product 1

HCID 178432483HCID 178432483, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-chloro-2-(2-chlorophenyl)-5,6-dimethylpyrimidine (31.14 g, 123 mmol) and 5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine (19.65 g, 129 mmol) in NMP (200 mL) was heated at 135° C. for 3 h 30 min. Then the mixture was concentrated in vacuo to around 100 mL. Then added sat aq. NaHCO3, water and EtOAc but a precipitate appeared in the organic layer. Filtered off this whole mixture and washed the residue with sat aq. NaHCO3, water and EtOAc and ether. Boiling ethanol was added to the residue with stirring and the pure target compound was filtered. The liquors were concentrated and this trituration procedure repeated 4 times to give the target (25 g, 55%) as a white solid.

Workup

  1. concentrationThen the mixture was concentrated in vacuo to around 100 mL
  2. additionThen added
  3. filtrationFiltered off this whole mixture
  4. washwashed the residue with sat aq. NaHCO3, water and EtOAc and ether
  5. additionBoiling ethanol was added to the residue
  6. filtrationthe pure target compound was filtered
  7. concentrationThe liquors were concentrated
  8. customto give the target (25 g, 55%) as a white solid

Sources & evidence

ORD record
ord-97bda7fc2d264e729f9967112a8ca605
Source dataset
uspto-grants-2013_08
Patent number
US08518953B2

Reaction notes

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