Triethylamine → 7-[N-(2'-Cyanobiphenyl-4-yl)methyl-N-methylamino]-5-ethylpyrazolo[1,5-a]pyrimidine

HRID 1450395Notes

Reaction equation

HRID 1450395 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH3:29])=[CH:23][CH:22]=1)#[N:14].C(N(CC)CC)C>C(O)C.O>[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[CH:23][C:24]([CH2:27][N:28]([C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=2)[CH3:29])=[CH:25][CH:26]=1)#[N:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 105354107-Chloro-5-ethylpyrazolo[1,5-a]pyrimidineHCID 15337416N-(2'-Cyanobiphenyl-4-yl)methyl-N-methyl amine

Product 1

HCID 153374177-[N-(2'-Cyanobiphenyl-4-yl)methyl-N-methylamino]-5-ethylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.8 g (10 mmol) of the chloro compound of Step B and 2.2 g (10 mmol) of the amine of Step C were dissolved in 60 ml ethanol and heated with reflux for 4 h. After addition of 3 ml triethylamine the heating was continued for an additional hour. The mixture was diluted with water and extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate, evaporated in vacuo, and the title compound obtained as an oil after purification by column chromatography on silica gel using ethyl acetate/hexane 9:1 as eluent,

Workup

  1. temperatureheated
  2. temperaturewith reflux for 4 h
  3. waitwas continued for an additional hour
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd4bab48dc174e2a94f52ddeb537026c
Source dataset
uspto-grants-1997_02
Patent number
US05602136

Reaction notes

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