Methanol → 2-Chloro-6-morpholinopyrimidine-4-carboxylic acid

HRID 1641266Notes

Reaction equation

HRID 1641266 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.O.CO.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 4356884Methyl 2-chloro-6-morpholin-4-ylpyrimidine-4-carboxylate

Product 1

HCID 184220792-Chloro-6-morpholinopyrimidine-4-carboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 2-chloro-6-morpholin-4-ylpyrimidine-4-carboxylate (0.30 g, 1.16 mmol) in a mixture of THF:H2O:MeOH (12 ml, 4:1:1) is stirred at room temperature for 24 hrs with lithium hydroxide (28 mg, 1.0 eq). The mixture is then evaporated to dryness to give 2-chloro-6-morpholin-4-ylpyrimidine-4-carboxylic acid as a solid (280 mg).

Workup

  1. customThe mixture is then evaporated to dryness

Sources & evidence

ORD record
ord-12a728ef9d6a489ebdb2bf3481648fa1
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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