Lithium hydroxide, monohydrate → 5-Methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1094738Notes

Reaction equation

HRID 1094738 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:20]([O:22]C)=[O:21].O[Li].O>C1COCC1.CO.O>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59842882Methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 598428265-Methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidYield 60.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (0.5 g, 1.5 mmol) was dissolved in a mixture of THF-MeOH—H2O (10 mL-3 mL-3 mL) followed by the addition of LiOH—H2O (0.250 g). The mixture was stirred at RT over night. The solvent evaporated and the residue was dissolved in 4 mL of water and then acidified with 2N HCl to pH˜3. The solid was filtered off, dried to gave 0.290 g of 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, in 60% yield.

Workup

  1. customThe solvent evaporated
  2. dissolutionthe residue was dissolved in 4 mL of water
  3. filtrationThe solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-0491fad61bfd4dc38fae0005b51cc2ef
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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