Water → HCID 22257958, compound

HRID 567924Notes

Reaction equation

HRID 567924 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([C:21]([O:23]CC)=[O:22])=[C:12]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:13][C:7]=2[N:6]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]1=[O:30].O>CO.O1CCCC1>[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([C:21]([OH:23])=[O:22])=[C:12]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:13][C:7]=2[N:6]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]1=[O:30]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 22258000HCID 22258000, compound

Product 1

HCID 22257958HCID 22257958, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1M Sodium hydroxide solution (7.5 ml) was added to a stirred solution of ethyl 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-phenylmethyl-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate (1.50 g) in methanol (7.5 ml) and tetrahydrofuran (15 ml). After 16 hours, further 1M sodium hydroxide solution (7.5 ml) was added and the solution was stirred at 50° C. for a further 8 hours. Water (100 ml) was added and the solution was washed with ether (100 ml). The aqueous phase was acidified by addition of concentrated hydrochloric acid and then extracted with ethyl acetate (2×100 ml). Undissolved solid in the organic extracts was filtered and dried in vacuo at 50° C. to give the title compound (1.00 g).

Workup

  1. washthe solution was washed with ether (100 ml)
  2. additionThe aqueous phase was acidified by addition of concentrated hydrochloric acid
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. filtrationwas filtered
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-4a0dc47b78374fdf9245a27b7bea4095
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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