Propylamine → 7-[N-(2'-Cyanobiphenyl-4-yl)methyl-N-propylamino]-5-methylpyrazolo[1,5-a]pyrimidine

HRID 1898894Notes

Reaction equation

HRID 1898894 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)#[N:2].C(N)CC.BrCC1C=CC(C2C=CC=CC=2C#N)=CC=1.Cl[C:41]1[N:46]2[N:47]=[CH:48][CH:49]=[C:45]2[N:44]=[C:43]([CH3:50])[CH:42]=1>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([C:41]2[N:46]3[N:47]=[CH:48][CH:49]=[C:45]3[N:44]=[C:43]([CH3:50])[CH:42]=2)[CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=1)#[N:2]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 104872877-Chloro-5-methylpyrazolo[1,5-a]pyrimidineHCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

Product 1

HCID 199759337-[N-(2'-Cyanobiphenyl-4-yl)methyl-N-propylamino]-5-methylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g (10.0 mmol) of N-(2'-cyanobiphenyl-4-yl)methyl-N-propyl amine (prepared from n-propylamine and 4-bromomethyl-2'-cyanobiphenyl by the method described in EP 490 820) and 1.8 g (10.7 mmol) 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine (prepared according to Y. Makisumi, Chem. Pharm. Bull. 1962, 10, 620) were heated with reflux in 20 ml dry ethanol for 4 h. The mixture was concentrated to halve of the volume in vacuo and cooled with ice, while the remaining starting amine crystallized. It was filtered with suction, and the rest of the solvent was removed. The title compound was obtained from the residue after column chromatography (silica gel, acetone/hexane 1:9 and 2:3) as a yellow oil.

Workup

  1. temperaturewere heated
  2. concentrationThe mixture was concentrated
  3. temperaturecooled with ice, while the remaining starting amine
  4. customcrystallized
  5. filtrationIt was filtered with suction
  6. customthe rest of the solvent was removed

Sources & evidence

ORD record
ord-b9ba051b8e2647168e11a860c3b59d39
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

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