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

HRID 2194470Notes

Reaction equation

HRID 2194470 reaction equation
[CH3:1][O:2][C:3](=[O:29])[NH:4][C:5]1[C:6]([NH2:28])=[N:7][C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[N:13]=2)=[N:9][C:10]=1[NH2:11].[H-].[Na+].I[CH3:33].Cl>CN(C)C=O>[NH2:11][C:10]1[C:5]([N:4]([CH3:33])[C:3](=[O:29])[O:2][CH3:1])=[C:6]([NH2:28])[N:7]=[C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[N:13]=2)[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46700769Methyl[4,6-diamino-2-(1-cyclohexylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]carbamate

Product 1

HCID 46830430Methyl N-[4,6-diamino-2-(1-cyclohexylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24 mg (61 μmol) of the compound of Example 1 were initially charged in 1 ml of dimethylformamide, and about 2.7 mg (70 μmol) of sodium hydride (60% in mineral oil) were added. The resulting mixture was stirred at RT for 10 min, 6 μl (9 μmol) of iodomethane were then added and the reaction was stirred overnight. 0.5 ml of 1N hydrochloric acid was added, and the entire mixture was separated by HPLC (Method 5). The appropriate fractions were concentrated on a rotary evaporator, and the residue was dried under high vacuum. This gave 8 mg (32% of theory) of the target compound.

Workup

  1. stirringthe reaction was stirred overnight
  2. customthe entire mixture was separated by HPLC (Method 5)
  3. concentrationThe appropriate fractions were concentrated on a rotary evaporator
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-dd81c965138940c6aece98d6e7d744b9
Source dataset
uspto-grants-2012_12
Patent number
US08334291B2

Reaction notes

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