Ammonia → 7-(2-Aminoethylamino)-2,5-dimethyl-3-(4-chloro-2,6-dimethylphenyl)-pyrazolo[1,5-a] pyrimidine

HRID 1016451Notes

Reaction equation

HRID 1016451 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:20])[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[CH:3]=1.[CH2:22]([NH2:25])[CH2:23][NH2:24].N.C(Cl)Cl>CC#N.CO>[NH2:24][CH2:23][CH2:22][NH:25][C:2]1[N:7]2[N:8]=[C:9]([CH3:20])[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 184069827-Chloro-2,5-dimethyl-3-(4-chloro-2,6-dimethylphenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 184070017-(2-Aminoethylamino)-2,5-dimethyl-3-(4-chloro-2,6-dimethylphenyl)-pyrazolo[1,5-a] pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Dissolve 7-chloro-2,5-dimethyl-3-(4-chloro-2,6-dimethylphenyl)-pyrazolo[1,5-a] pyrimidine in 25 mL CH3CN, then add excess ethylenediamine (5 mL) and heat to 80° C. for 3-6 h under N2 with attached reflux condenser. (TLC; product diamine Rf=0.5, aryl chloride Rf=1.0; [10% (2.0M NH3 in MeOH)/90% CH2Cl2] as eluent). Cool to ambient temperature and evaporate to yellow oil. Partition between CH2Cl2 (50 mL) and 1.0 N NaOH (50 mL), and extract aqueous layer 2×30 mL CH2Cl2. Pool organic layers, dry over Na2SO4, filter and evaporate to yellow-white foam (1.25 g). Use without further purification. LCMS=344.4 (MH+); 342.3 (M−).

Workup

  1. customevaporate to yellow oil
  2. customPartition between CH2Cl2 (50 mL) and 1.0 N NaOH (50 mL)
  3. extractionextract aqueous layer 2×30 mL CH2Cl2
  4. dry with materialPool organic layers, dry over Na2SO4
  5. filtrationfilter
  6. customevaporate to yellow-white foam (1.25 g)
  7. customUse without further purification

Sources & evidence

ORD record
ord-e6ff041fd1a84426be5bc129f7f7787d
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

Loading…