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

HRID 2280745Notes

Reaction equation

HRID 2280745 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-e32bd460e49d4c8d8d269bc8858200b1
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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