Chloroacetamide → HCID 57503713, compound

HRID 556395Notes

Reaction equation

HRID 556395 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:18])[C:3]=1[C:19]#[N:20].Cl[CH2:22][C:23]([NH2:25])=[O:24].CC[O-].[Na+]>C(O)C>[NH2:20][C:19]1[C:3]2[C:4]([CH3:18])=[N:5][C:6]([C:8]3[CH:9]=[CH:10][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=3)=[N:7][C:2]=2[S:1][C:22]=1[C:23]([NH2:25])=[O:24]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 2723922Sodium ethoxideHCID 178432561HCID 178432561, compound

Product 1

HCID 57503713HCID 57503713, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.0 g (14 mmol) 6-mercapto-4-methyl-2-(4-iso-propoxy-phenyl)-pyrimidine-5-carbonitrile and 1.6 g (17 mmol) 2-chloroacetamide are suspended in 100 ml ethanol and 1.9 g (28 mmol) sodium ethylate is admixed. The reaction mixture is refluxed for 3 h. It is filtrated, washed with ethanol and water and dried. 1.5 g (31%) 5-amino-4-methyl-2-(4-iso-propoxy-phenyl)-thieno[2,3-d]pyrimidine-6-carboxamide is obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. filtrationIt is filtrated
  3. washwashed with ethanol and water
  4. customdried

Sources & evidence

ORD record
ord-ea353f2c8aac42258941fa9678b4eabc
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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