Dimethylformamide → HCID 53948418, compound

HRID 1884908Notes

Reaction equation

HRID 1884908 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[N:19]=[C:18]([Cl:20])[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH:5]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH2:33](I)[CH3:34]>O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[N:19]=[C:18]([Cl:20])[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH2:33][CH3:34])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178497917HCID 178497917, compound

Product 1

HCID 53948418HCID 53948418, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A 750 ml flask is charged with 25.4 g (83.5 mmol) of 3-(2-chloro-9H-purin-6-yl-amino)-benzoic acid methyl ester, 12.95 g (93.7 mmol) of K2CO3 and 360 ml of DMF. The mixture is stirred at RT for 30 min, then 35.8 ml (443 mmol) ethyliodide are added under slight cooling. After completion, the mixture is poured into water/EtOAc (1.2 l each). The aqueous layer is extracted with ethyl acetate (2 fold). The combined organic layers are washed with water and brine, dried (Na2SO4), filtered and concentrated. After purification by chromatography (silica gel, EtOAc) the desired product, 3-(2-chloro-9-ethyl-9H-purin-6-yl-amino)benzoic acid methyl ester, (19.1 g, 69% yield) is obtained; Rf=0.25; (EtOAc); m.p. 148° C.; ESI-MS: 332 (M+H)+.

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate (2 fold)
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customAfter purification by chromatography (silica gel, EtOAc) the desired product

Sources & evidence

ORD record
ord-06c7d7c2ecb74c4bac8b76874b91ac06
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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