Water → Ammonia

HRID 362310Notes

Reaction equation

HRID 362310 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]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:35]1[CH:39]=[CH:38][N:37]=[C:36]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][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]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 539498265-(3-Benzyloxyphenyl)-7-[3-(2-chloroethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidineHCID 178507081HCID 178507081, compound

Product 2

HCID 222AmmoniaHCID 541929665-(3-Benzyloxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of 5-(3-benzyloxyphenyl)-7-[3-(2-chloroethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine (Ex. 153) and 0.46 g of imidazolyl sodium are heated to 50° C. in 45 ml of DMF and the mixture is stirred for 15 h. The mixture is then cooled to RT and treated with water, extracted 3 times with ethyl acetate and concentrated. After chromatography on silica gel (methylene chloride/methanol containing 5% of about 5N ammonia in methanol), 5-(3-benzyloxyphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an Rf=0.4 (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-37b491b51311497f9888a9b8dfa6c9c3
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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