Acrolein → 3-[5-(3-methyl-4-isothiazolyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]propanal

HRID 1925043Notes

Reaction equation

HRID 1925043 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=2)=[CH:5][S:4][N:3]=1.C(N(CC)CC)C.[CH:22]([CH:24]=[CH2:25])=[O:23]>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[N:11]([CH2:25][CH2:24][CH:22]=[O:23])[CH:12]=2)=[CH:5][S:4][N:3]=1

Participants

5

Reactant 3

HCID 7847Acrolein2×HCID 8471TriethylamineHCID 594483785-(3-methyl-4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 594483533-[5-(3-methyl-4-isothiazolyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]propanal

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-methyl-4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione (Pre 47, 0.126 mmol) was dissolved in N,N-Dimethylformamide (DMF) (1 ml). TRIETHYLAMINE (0.021 ml, 0.151 mmol) was added and the mixture was stirred at room temperature for 5 minutes. Acrolein (8.42 μl, 0.126 mmol) was added and the mixture was stirred at room temperature monitoring the reaction progression by LCMS. After 7 hrs Acrolein (3 μl) was added and the mixture was stirred at rt overnight.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. stirringthe mixture was stirred at rt overnight

Sources & evidence

ORD record
ord-80d5e21ef2f24596b8d442bf142bea78
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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