Water → 3-(2-(3,5-Bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1094711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094711
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:31])[CH2:15][N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH3:30])=[C:24]([C:26]([O:28]C)=[O:27])[S:25][C:19]=3[N:18]=[CH:17]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.O.[OH-].[Li+]>C1COCC1.CO>[F:32][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:31])[CH2:15][N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH3:30])=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:19]=3[N:18]=[CH:17]2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59842865Methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Produkt 1

HCID 453959523-(2-(3,5-Bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, (3.3 g, 6.75 mmol) in THF (30 mL), MeOH (10 mL), and H2O (10 mL) was added lithium hydroxide monohydrate (1.42 g, 33.8 mmol). The reaction mixture was then 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 1.9 g of 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (yield: 59%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8e572dbd0ede49cbb7c60f542184e73a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133998B2

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