Water → HCID 59842844, compound

HRID 1094705Notes

Reaction equation

HRID 1094705 reaction equation
[C:1]([NH:5][C:6](=[O:23])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:22])=[C:16]([C:18]([O:20]C)=[O:19])[S:17][C:11]=2[N:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].O.O.[OH-].[Li+]>C1COCC1.CO>[C:1]([NH:5][C:6](=[O:23])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:22])=[C:16]([C:18]([OH:20])=[O:19])[S:17][C:11]=2[N:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59842876Methyl 3-(2-(tert-butylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 59842844HCID 59842844, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(2-(tert-butylamino)-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 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 1.8 g of 3-(2-(tert-butylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid (yield: 55%).

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-c56a098761c94495baf06c0550ee1a6e
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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