Ethanol → 1-(2-aminoethyl)-6-(2,4-dimethoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one hydrochloride

HRID 75542Notes

Reaction equation

HRID 75542 reaction equation
CCO.C([Cl:7])(=O)C.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[C:18]1[N:23]([CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[C:22](=[S:34])[NH:21][C:20](=[O:35])[CH:19]=1>CCOC(C)=O>[ClH:7].[NH2:26][CH2:25][CH2:24][N:23]1[C:18]([C:11]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=2[O:9][CH3:8])=[CH:19][C:20](=[O:35])[NH:21][C:22]1=[S:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 86684681tert-butyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)ethylcarbamate

Product 1

HCID 866846801-(2-aminoethyl)-6-(2,4-dimethoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one hydrochlorideYield 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EtOH (50 mL, 860 mmol) in EtOAc (390 mL), cooled in an ice/water bath, was slowly added acetyl chloride (55 mL, 770 mmol) over 3 minutes. After 5 minutes the cooling bath was removed, and after stirring for 45 min, the solution was added to tert-butyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)ethylcarbamate (31.7 g, 77.8 mmol). A suspension formed over time, and after stirring for 5 h, the solid was collected by vacuum filtration, rinsing with EtOAc. The solid was pulled dry and dried further under vacuum to afford 26.6 g (99.3%) of the desired product as a colorless solid.

Workup

  1. customover 3 minutes
  2. customAfter 5 minutes the cooling bath was removed
  3. customA suspension formed over time
  4. stirringafter stirring for 5 h
  5. filtrationthe solid was collected by vacuum filtration
  6. washrinsing with EtOAc
  7. customThe solid was pulled dry
  8. customdried further under vacuum

Sources & evidence

ORD record
ord-745ddc4e06b04ea3ae82eda8d177e437
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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