Lithium hydroxide, monohydrate → 6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid

HRID 1746651Notes

Reaction equation

HRID 1746651 reaction equation
[CH:1]1([N:7]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([O:16]C)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>C1COCC1.CCO.O>[CH:1]1([N:7]([CH2:18][CH:19]2[CH2:20][CH2:21]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59446889Methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate2×

Product 1

HCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 12, 4.14 g; 14.3 mmol) in THF/EtOH/H2O (3/2/1, 120 ml) was treated with an aqueous solution of lithium hydroxide monohydrate (42.9 ml; 1.00 M; 42.9 mmol) at ambient temperature. After 1 hour, the organic solvents were evaporated in vacuo, the remaining aqueous layer was acidified with HCl (1 N) until pH=6 and extracted with DCM (4×50 ml). The combined organic layers were dried over MgSO4 and evaporated to dryness to give the title compound as an off-white solid (3.64 g, 92.5%).

Workup

  1. customthe organic solvents were evaporated in vacuo
  2. extractionextracted with DCM (4×50 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-52efaf011f3940f89891605764ba5cc8
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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