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

HRID 379581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379581
[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]

Komponenten

6

Edukt 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

Produkt 1

HCID 52825241,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acidAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-acfa6d1da0584a3da611eaf0e3b8f6be
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300334B1

Notizen zur Reaktion

Wird geladen…