Water → Ammonia

HRID 362312Notes

Reaction equation

HRID 362312 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34]Cl)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:36]1[CH:40]=[CH:39][N:38]=[C:37]1[Na].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][N:36]4[CH:40]=[CH:39][N:38]=[CH:37]4)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 539591615-(3-Benzyloxyphenyl)-7-[3-(3-chloro-1-propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidineHCID 178507081HCID 178507081, compound

Product 2

HCID 222AmmoniaHCID 702056565-(3-Benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of 5-(3-benzyloxyphenyl)-7-[3-(3-chloro-1-propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine and 0.33 g of imidazolyl sodium are heated to 50° C. in 30 ml of DMF and the mixture is stirred overnight. It is then cooled to RT, the solvent is stripped off in an RE and the mixture is treated with water, extracted 3 times with ethyl acetate and concentrated. 5-(3-benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine, (Rf=0.44, silica gel, methylene chloride/methanol containing 5% of about 5N ammonia in methanol 9:1) is obtained.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e5aec6a4fdbb4e4585003e7f6ace6f0a
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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