Triphosgene → 6-Methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 877017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877017
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.O>[CH3:10][C:4]1[S:3][C:2]2[NH:1][C:12](=[O:14])[NH:9][C:7](=[O:8])[C:6]=2[CH:5]=1

Komponenten

5

Edukt 2

HCID 94429TriphosgeneHCID 136257322-Amino-5-methylthiophene-3-carboxamide

Produkt 1

HCID 127242076-Methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of Step 2 intermediate (16.5 g, 94.82 mmol) in dry THF (316 ml) was added triphosgene (14.07 g, 47.41 mmol) and the mixture was refluxed for overnight under nitrogen atmosphere. The mixture was cooled to room temperature and diluted with water (200 ml) under stirring. The solid precipitated out was collected by filtration and dried to give 13.8 g of the desired product; 1H NMR (300 MHz, DMSO-d6) δ 2.36 (s, 3H), 6.82 (s, 1H), 11.07 (br. s, 1H), 11.79 (br. s, 1H).

Aufarbeitung

  1. temperaturethe mixture was refluxed for overnight under nitrogen atmosphere
  2. customThe solid precipitated out
  3. filtrationwas collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-29ce839f16be474a976c95bc9faa2150
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987278B2

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