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

HRID 857936Notes

Reaction equation

HRID 857936 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.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:18][C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([CH3:28])=[C:21]([CH2:29]Cl)[N:20]=1>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]([CH2:29][C:21]3[C:22]([CH3:28])=[C:23]([O:26][CH3:27])[C:24]([CH3:25])=[C:19]([Cl:18])[N:20]=3)[N:10]=[CH:11][C:3]=12

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 218828892-Chloro-6-(chloromethyl)-4-methoxy-3,5-dimethylpyridine

Product 1

HCID 588781164-Chloro-1-(6-chloro-4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (124 mg), Cs2CO3 (392 mg) and crude 2-chloro-6-chloromethyl-4-methoxy-3,5-dimethyl-pyridine (200 mg) in DMF (2 ml) was heated to 80° C. for 1 h, diluted with EtOAc and washed with water. Concentration and purification by preparative TLC (EtOAc) gave the title compound. R.t. 6.43 min. 1H-NMR (CDCl3) δ 7.86 (s, 1H), 5.48 (s, 2H), 5.37 (s, 2H), 3.71 (s, 3H), 2.27 (s, 3H), 2.15 (s, 3H).

Workup

  1. washwashed with water
  2. concentrationConcentration and purification by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-e091141bf5ad42fda4aa5a4240fce9d6
Source dataset
uspto-grants-2006_12
Patent number
US07148228B2

Reaction notes

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