Water → 1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

HRID 379581

Reaction equation

HRID 379581 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][S:13][C:7]=2[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:5]1=[O:23].O>CO.O1CCCC1>[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([C:14]([OH:16])=[O:15])=[CH:12][S:13][C:7]=2[N:6]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:5]1=[O:23]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 5282568Ethyl 3-methyl-1-(2-methylpropyl)-2,4-dioxo-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 52825241,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acidYield 92.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2M Sodium hydroxide solution (30 ml) was added to a solution of ethyl 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate (16.13 g) in methanol (25 ml) and tetrahydrofuran (50 ml). After 6 hours, further 2M sodium hydroxide solution (30 ml) was added. After a further 2 hours, water (500 ml) was added and the mixture was extracted with ether (250 ml). The aqueous layer extracts were acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×250 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was redissolved in tetrahydrofuran (100 ml) and evaporated to give the subtitle compound (13.58 g) as a solid.

Workup

  1. waitAfter a further 2 hours
  2. extractionthe mixture was extracted with ether (250 ml)
  3. extractionextracted with ethyl acetate (3×250 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was redissolved in tetrahydrofuran (100 ml)
  8. customevaporated

Sources & evidence

ORD record
ord-acfa6d1da0584a3da611eaf0e3b8f6be
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Linked notes

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