Diisopropylethylamine → 4-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide

HRID 2280745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280745
[CH:1]([NH:4][C:5]1[C:10]([C:11](O)=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2].C[N:17](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]([NH:4][C:5]1[C:10]([C:11]([NH2:17])=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 127840854-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic AcidHCID 12820921Azane;hydrochloride

Produkt 1

HCID 709813214-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (8.38 g, 36.9 mmol) and HATU (21.03 g, 55.3 mmol) were combined in a 250 mL round-bottomed flask followed by the addition of DMF (92 mL). After that ammonia hydrochloride (9.86 g, 184 mmol) and DIEA (32 mL, 184 mmol) were added and the mixture was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and water (150 mL) was added. The resulting suspension was filtered, washed with water and dried under high vacuum overnight to afford 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide (8 g, 35.4 mmol, 96% yield); MS (ESI) m/z 227.4 [M+1]+.

Aufarbeitung

  1. concentrationThe solvent was concentrated under reduced pressure and water (150 mL)
  2. additionwas added
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water
  5. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-e32bd460e49d4c8d8d269bc8858200b1
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139534B2

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