Potassium Carbonate → 2-[1-(8-Propyl-[1,2,4]triazolo[1,5-C]pyrimidin-7-ylmethyl)-1H-imidazol-2-YL]-nicotinonitrile

HRID 916663Notes

Reaction equation

HRID 916663 reaction equation
Br[CH2:2][C:3]1[N:8]=[CH:7][N:6]2[N:9]=[CH:10][N:11]=[C:5]2[C:4]=1[CH2:12][CH2:13][CH3:14].[NH:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:12]([C:4]1[C:5]2[N:6]([N:9]=[CH:10][N:11]=2)[CH:7]=[N:8][C:3]=1[CH2:2][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 552537712-(1H-imidazol-2-yl)-nicotinonitrileHCID 575033117-Bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 111753352-[1-(8-Propyl-[1,2,4]triazolo[1,5-C]pyrimidin-7-ylmethyl)-1H-imidazol-2-YL]-nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 169 (56 mg, 0.22 mmol), 170 (42 mg, 0.25 mmol) and K2CO3 (138 mg) in DMF (4 mL) is stirred at room temperature overnight. Solvent is removed in vacuo. Water (10 mL) is added and the mixture is extracted with ethyl acetate (3×25 mL). The combined organic layers are dried and solvent removed. The crude is purified by PTLC (5% MeOH in methylene chloride) to give the title product (167) as a solid. 1H NMR 9.13 (s, 1H), 8.64–8.66 (m, 1H), 8.36 (s, 1H), 8.07–8.10 (m, 1H), 7.29–7.34 (m, 1H), 7.32 (s, 1H), 7.23 (s, 1H), 5.94 (s, 2H), 3.02–3.08 (m, 2H) 1.66–1.74 (m, 2H), 1.00 (t, 3H).

Workup

  1. customSolvent is removed in vacuo
  2. additionWater (10 mL) is added
  3. extractionthe mixture is extracted with ethyl acetate (3×25 mL)
  4. customThe combined organic layers are dried
  5. customsolvent removed
  6. customThe crude is purified by PTLC (5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-d775d7910ee94abfb145ac3e7a7b73c6
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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