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

HRID 1094701Notes

Reaction equation

HRID 1094701 reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[C:4](=[O:21])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([CH3:20])=[C:14]([C:16]([O:18]C)=[O:17])[S:15][C:9]=2[N:8]=[CH:7]1)[CH3:2].O.O.[OH-].[Li+]>C1COCC1.CO>[CH2:22]([N:3]([CH2:1][CH3:2])[C:4](=[O:21])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([CH3:20])=[C:14]([C:16]([OH:18])=[O:17])[S:15][C:9]=2[N:8]=[CH:7]1)[CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 1680569Methyl 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 44267003-(2-(Diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (3.3 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 1.6 g of 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (yield: 50%).

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-68c9e498d3964f2e8b2173bd1235e005
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

Loading…