Dimethylformamide → 4-Chloro-1-(4-chloro-3,5-dimethyl-pyridin-2-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 857937Notes

Reaction equation

HRID 857937 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.[Cl:12][C:13]1[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([CH2:20]Cl)[C:14]=1[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([CH2:20][C:15]3[C:14]([CH3:22])=[C:13]([Cl:12])[C:18]([CH3:19])=[CH:17][N:16]=3)[N:10]=[CH:11][C:3]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 110196374-chloro-2-chloromethyl-3,5-dimethylpyridineHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 587627964-Chloro-1-(4-chloro-3,5-dimethyl-pyridin-2-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (158 mg), crude 4-chloro-2-chloromethyl-3,5-dimethyl-pyridine (204 mg), Cs2CO3 (660 mg) and DMF was heated to 80° C. for 1.5 h, diluted with EtOAc and washed with water. The crude material was concentrated and suspended in MeOH/DCM. Filtration gave a 2:1 mixture of regioisomers which was further purified by preparative silica gel plate (EtOAc 100%). The major (less polar) isomer corresponded to the title compound. R.t. 5.45 min. 1H-NMR (CDCl3) δ 8.22 (s, 1H), 7.90 (s, 1H), 5.57 (s, 2H), 5.28 (s, 2H), 2.43 (s, 3H), 2.31 (s, 3H).

Workup

  1. washwashed with water
  2. concentrationThe crude material was concentrated
  3. filtrationFiltration
  4. customgave
  5. additiona 2:1 mixture of regioisomers which
  6. customwas further purified by preparative silica gel plate (EtOAc 100%)
  7. custom5.45 min

Sources & evidence

ORD record
ord-14f83fba12cb4ecebea56f986d854cac
Source dataset
uspto-grants-2006_12
Patent number
US07148228B2

Reaction notes

Loading…