N,N-Diethylaniline → Methyl 4-chloro-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylate

HRID 510075Notes

Reaction equation

HRID 510075 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18](O)[C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:16][N:15]=2)=[N:6]1.P(Cl)(Cl)([Cl:31])=O.CCN(C1C=CC=CC=1)CC>>[Cl:31][C:18]1[C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:16][N:15]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:25]=[CH:26][CH:27]=[CH:28][C:2]=3[F:1])[N:6]=2)[N:19]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178498784HCID 178498784, compound

Product 1

HCID 86720049Methyl 4-chloro-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylate

Procedure

6.54 g (17.2 mmol) of methyl 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-hydroxypyrimidine-5-carboxylate (example 105A) were taken up in 26.5 ml (284 mmol) of phosphoryl chloride. Then 5.95 g (34.5 mmol) of diethylaniline were added and the mixture was reacted at 90° C. for 60 min. After cooling, the precipitate formed was filtered off and washed with water. Then it was dried under high vacuum. Thus, 6.11 g (78% of theory) of the target compound were obtained.

Workup

  1. customthe mixture was reacted at 90° C. for 60 min
  2. temperatureAfter cooling
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customThen it was dried under high vacuum
  7. customThus, 6.11 g (78% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-ec40b1581de64628856effbedba8f011
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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