Dimethylformamide → HCID 20185099, compound

HRID 2309360Notes

Reaction equation

HRID 2309360 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[S:8][C:6]=2[N:7]=1.[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH:27]([CH3:31])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].CN(C)C=O>O.C1C=CC=CC=1>[CH2:18]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[N:3]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]3[CH:10]=[C:9]([CH3:11])[S:8][C:6]=3[N:7]=2)[CH:27]([CH3:31])[CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 19660Carbonate IonHCID 27275201-Benzyl-3-methylpiperazineHCID 13557183HCID 13557183, compound

Product 1

HCID 20185099HCID 20185099, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 3 g of 2-chloro-6-methyl-4-phenyl-thieno[2,3-d]pyrimidine, 2.2 g of 1-benzyl-3-methylpiperazine, 1.1 g of sodum carbonate and 4 ml of dimethylformamide is reacted under reflux for 3 hours. After cooling, 80 ml of benzene and 80 ml of water are added and two layers are separated. The benzene layer is washed twice with 100 ml of water and then with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After distilling off benzene, purification of the product by silica gel chromatography using 180 g of silica gel and n-hexane/ethyl acetate (10:1) as an eluent is carried out. There is obtained 4.3 g of oily 2-(4-benzyl-2-methylpiperazinyl)-6-methyl-4-phenyl-thieno[2,3-d]pyrimidine.

Workup

  1. customis reacted
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customtwo layers are separated
  5. washThe benzene layer is washed twice with 100 ml of water
  6. dry with materialwith saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  7. distillationAfter distilling off
  8. custombenzene, purification of the product by silica gel chromatography

Sources & evidence

ORD record
ord-809c8fc7a5314bbdb583288528b07513
Source dataset
uspto-grants-1987_09
Patent number
US04695568

Reaction notes

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