Dimethylformamide → 3-Bromo-1-methyl-N*4*-(2-morpholin-4-yl-ethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
Reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:12])=[N:8][C:9]=2Cl)[N:4]([CH3:13])[N:3]=1.[N:14]1([CH2:20][CH2:21][NH2:22])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CN(C=O)C>C(Cl)Cl.O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:12])=[N:8][C:9]=2[NH:22][CH2:21][CH2:20][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:4]([CH3:13])[N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
3-Bromo-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 14) (750 mg, 2.8 mmol), 2-(4-morpholinyl)ethylamine (0.44 ml, 3.3 mmol) and DMF (30 ml) are mixed together and heated to 50° C. overnight. After cooling to room temperature the reaction mixture is diluted with DCM (60 ml) and water (40 ml) and the aqueous portion is extracted with a further 40 ml DCM. The organic portions are combined, dried over MgSO4, filtered and concentrated in vacuo. The crude residue is dry loaded onto silica and purification by flash chromatography eluting with DCM then MeOH:DCM (5:95) affords the title compound.
Workup
- temperatureAfter cooling to room temperature the reaction mixture
- extractionthe aqueous portion is extracted with a further 40 ml DCM
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- dry with materialThe crude residue is dry loaded onto silica and purification by flash chromatography
- washeluting with DCM
Sources & evidence
- ORD record
- ord-0ebf81ec4e4a41c997ca120b1443d4e9
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901134B2
Reaction notes
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