Methanol → 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylic acid

HRID 1853052Notes

Reaction equation

HRID 1853052 reaction equation
[C:1]([CH2:3][CH:4]([N:8]1[CH:12]=[C:11]([C:13]2[N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[CH:16]=[C:15]([C:22]([O:24]C)=[O:23])[N:14]=2)[CH:10]=[N:9]1)[CH:5]1[CH2:7][CH2:6]1)#[N:2].CO.[Li+].[OH-]>>[C:1]([CH2:3][CH:4]([N:8]1[CH:12]=[C:11]([C:13]2[N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[CH:16]=[C:15]([C:22]([OH:24])=[O:23])[N:14]=2)[CH:10]=[N:9]1)[CH:5]1[CH2:6][CH2:7]1)#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67456699methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

Product 1

HCID 674585015-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylic acid

Procedure

In a 20 mL flask, methyl 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (0.127 g, 0.378 mmol) was dissolved in MeOH (1.89 mL, 0.378 mmol) and treated with LiOH (0.755 mL, 0.755 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, then concentrated down to dryness and used directly in the next step. MS (apci) m/z=323.1 (M+H).

Workup

  1. concentrationconcentrated down to dryness

Sources & evidence

ORD record
ord-5cb4293809754052b6576870ca38e577
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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