2-Methoxyethanol → HCID 58485838, compound

HRID 1524339Notes

Reaction equation

HRID 1524339 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][CH2:19][CH2:20][OH:21]>>[CH3:17][O:18][CH2:19][CH2:20][O:21][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 58485838HCID 58485838, compound

Procedure

1.1 A suspension of 1.00 g (6.32 mmol) of 4-chloro-7H-pyrrolo[2,3-d]-pyrimidine and 5.20 g (15.8 mmol) of caesium carbonate in 30 ml of 2-methoxy-ethanol is heated under reflux for 24 hours. The reaction mixture is adsorbed onto kieselguhr and chromatographed on a silica-gel column with dichloromethane/methanol/aqueous ammonia (100:1:1) as eluent, giving 4-(2-methoxyethoxy)-7H-pyrrolo[2,3-d]pyrimidine as colourless crystals; m.p. 137-139° C.;

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. customchromatographed on a silica-gel column with dichloromethane/methanol/aqueous ammonia (100:1:1) as eluent

Sources & evidence

ORD record
ord-68bf77c883d74eacb820e0431d9c0bc3
Source dataset
uspto-grants-2015_07
Patent number
US09079910B2

Reaction notes

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