Diethylamine → HCID 18924858, compound

HRID 1288823Notes

Reaction equation

HRID 1288823 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:6]2[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:7]=2[N:8]=1.[CH2:24]([NH:26][CH2:27]C)C>ClCCl>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:5]2[C:6]3[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:7]=3[N:8]=[C:3]([CH2:2][N:26]([CH3:27])[CH3:24])[N:4]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 18924851HCID 18924851, compound

Product 1

HCID 18924858HCID 18924858, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidine (1.0 g), diethylamine (1.2 ml) and dichloromethane (30 ml) was stirred for 16 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was dissolved in ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-methanol (5:1, v/v), was obtained 4-(3,4-dimethoxyphenyl)-5,6-dimethyl-2-(N,N-dimethylamino-methyl)thieno[2,3-d]pyrimidine (0.49 g, 44%). Recrystallization from isopropyl ether gave colorless prisms, m.p.118°-120° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure, which
  3. dissolutionwas dissolved in ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off
  7. washFrom the fraction eluted with ethyl acetate-methanol (5:1

Sources & evidence

ORD record
ord-dd322dead33a4bf28942748923428705
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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