Dimethylformamide → HCID 58762794, compound

HRID 857935Notes

Reaction equation

HRID 857935 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.Cl[CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].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]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[N:10]=[CH:11][C:3]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 58762794HCID 58762794, compoundYield 17.2%

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 (1.76 g), 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine hydrochloride (3.70 g), K2CO3 (5.17 g), and DMF (20 ml) was heated to 80° C. for 30 min, diluted with EtOAc, washed with water and brine, concentrated, and purified by flash chromatography to give the title compound as a white solid (0.57 g). R.t. 4.46 min. 1H-NMR (CDCl3) δ 8.10 (s, 1H), 7.89 (s, 1H), 5.53 (2H), 5.24 (br. s, 2H), 3.74 (s, 3H), 2.27 (s, 3H), 2.22 (s, 3H).

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8e707cb75ce446c09388e22b47f93c4e
Source dataset
uspto-grants-2006_12
Patent number
US07148228B2

Reaction notes

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