Acetonitrile → HCID 22048085, compound

HRID 1830577Notes

Reaction equation

HRID 1830577 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.C(#N)C.Cl[C:20]1[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=[C:22]([S:29][CH3:30])[C:21]=1[C:31]#[N:32]>O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:20]2[N:25]3[N:26]=[CH:27][CH:28]=[C:24]3[N:23]=[C:22]([S:29][CH3:30])[C:21]=2[C:31]#[N:32])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 220480807-Chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile

Product 1

HCID 22048085HCID 22048085, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 460 mg of 4-picolylamine, 430 mg of triethylamine and 1 ml of acetonitrile was dropwise added to 950 mg of 7-chloro-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile and 20 ml of acetonitrile under cooling with ice, followed by stirring for about 1 hour. After completion of the reaction, about 80 ml of water was added thereto, and the precipitated crystals were collected by filtration, washed with water and dried to obtain crude crystals. The crude crystals were purified by silica gel column chromatography to obtain 970 mg of 7-(4-pyridylmethyl)amino-5-methylthiopyrazolo[1,5-a]pyrimidine-6-carbonitrile (compound No. 3) having a melting point of from 153 to 154° C.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried
  6. customto obtain crude crystals
  7. customThe crude crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-063ee40dd54c4fe2815b2952630b9b8a
Source dataset
uspto-grants-2006_06
Patent number
US07067520B2

Reaction notes

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