Hydrochloric Acid → Methyl[4,6-diamino-2-(1-cyclohexylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]carbamate

HRID 2194468Notes

Reaction equation

HRID 2194468 reaction equation
[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[C:6]([NH2:21])=[N:7][C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[N:9][C:10]=1[NH2:11].Br[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[C:10]([NH2:11])=[N:9][C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:13]=2)=[N:7][C:6]=1[NH2:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 178502011Methyl[4,6-diamino-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]carbamate

Product 1

HCID 46700769Methyl[4,6-diamino-2-(1-cyclohexylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

330 mg (1.1 mmol) of the compound of Example 1A and 212 mg (1.2 mmol) of bromomethylcyclohexane were initially charged in 5 ml of dimethylformamide, 389 mg (1.2 mmol) of cesium carbonate were added and the resulting mixture was stirred at RT overnight. 0.5 ml of 1N hydrochloric acid was added, and the entire solution was separated by HPLC (Method 5). The appropriate fractions were freed from volatile components on a rotary evaporator, and the residue was dried under high vacuum. This gave 60 mg (19% of theory) of the target compound.

Workup

  1. customthe entire solution was separated by HPLC (Method 5)
  2. customThe appropriate fractions were freed from volatile components on a rotary evaporator
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-bb5a41302e824ec49e287918d18f9e2c
Source dataset
uspto-grants-2012_12
Patent number
US08334291B2

Reaction notes

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