Water → 3-(2-(Cyclohexylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1094708Notes

Reaction equation

HRID 1094708 reaction equation
[CH:1]1([NH:7][C:8](=[O:25])[CH2:9][N:10]2[C:15](=[O:16])[C:14]3[C:17]([CH3:24])=[C:18]([C:20]([O:22]C)=[O:21])[S:19][C:13]=3[N:12]=[CH:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[OH-].[Li+]>C1COCC1.CO>[CH:1]1([NH:7][C:8](=[O:25])[CH2:9][N:10]2[C:15](=[O:16])[C:14]3[C:17]([CH3:24])=[C:18]([C:20]([OH:22])=[O:21])[S:19][C:13]=3[N:12]=[CH:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 1093519Methyl 3-(2-(cyclohexylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 234104873-(2-(Cyclohexylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(2-(cyclohexylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (3.6 g, 10 mmol) in THF (30 mL), MeOH (10 mL), and H2O (10 mL) was added lithium hydroxide monohydrate (1.26 g, 30 mmol). The reaction mixture was then stirred at RT overnight. The reaction mixture was concentrated, diluted with H2O (30 mL) and washed with DCM (2×30 mL). The aqueous layer was acidified (pH˜2) with 1M HCl and the resultant precipitate was filtered and dried to give 1.7 g of 3-(2-(cyclohexylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (yield: 52%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O (30 mL)
  3. washwashed with DCM (2×30 mL)
  4. filtrationthe resultant precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-d94b6cc2b9384fb9899f8bdbf461c66d
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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