Allylamine → N-Allyl-4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide

HRID 1783556Notes

Reaction equation

HRID 1783556 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11](Cl)=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2].[CH2:16]([NH2:19])[CH:17]=[CH2:18]>O1CCCC1.C(OCC)(=O)C>[CH2:16]([NH:19][C:11]([C:10]1[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]([S:14][CH3:15])=[N:8][CH:9]=1)=[O:12])[CH:17]=[CH2:18]

Participants

5

Reactant 2

HCID 7853AllylamineHCID 539636504-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride

Product 1

HCID 54231982N-Allyl-4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamideYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. suspension of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride in 10 mL of tetrahydrofuran is added 3.5 mL (46.2 mmol) of allylamine and 20 mL of tetrahydrofuran. The reaction suspension is allowed to warm briefly to room temperature, then stored at 0° C. overnight. The reaction mixture is diluted with ethyl acetate, washed with 1N HCl, a saturated solution of sodium bicarbonate, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated to give 2.1 g (51%) of the title compound:

Workup

  1. washwashed with 1N HCl
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-161ff308cde042ffb55afce2d51f1f15
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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