Water → HCID 70202784, compound

HRID 362323Notes

Reaction equation

HRID 362323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27]Cl)[CH:20]=3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[Na].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:16]([NH2:18])=[N:15][CH:14]=[N:13][C:12]=3[N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][N:29]4[CH:33]=[CH:32][N:31]=[CH:30]4)[CH:20]=3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 54140298HCID 54140298, compoundHCID 57373095Imidazole sodium

Product 1

HCID 70202784HCID 70202784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 g of 5-(3-methoxyphenyl)-7-[3-(2-chloro-1-ethoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine and 0.24 g of sodium imidazole are heated to 80° C. in 20 ml of DMF and stirred for 5 h. The mixture is then cooled to RT and treated with water, extracted 3 times with methylene chloride and concentrated. After chromatography on silica gel using methylene chloride/methanol 15:2 and crystallization from ether/methylene chloride, 5-(3-methoxy-phenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an m.p. of 138°-140° C. is obtained.

Workup

  1. extractionextracted 3 times with methylene chloride
  2. concentrationconcentrated
  3. custommethylene chloride/methanol 15:2 and crystallization from ether/methylene chloride, 5-(3-methoxy-phenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an m.p. of 138°-140° C.
  4. customis obtained

Sources & evidence

ORD record
ord-9b9d739e661b4cfb88f1650523485e43
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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