Potassium Carbonate → 6-[1-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-1H-imidazol-2-yl]-pyridine-2-carbonitrile

HRID 916666Notes

Reaction equation

HRID 916666 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:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=1.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:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 232080316-(1H-Imidazol-2-yl)picolinonitrileHCID 575033117-Bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 114279106-[1-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-1H-imidazol-2-yl]-pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 169 (97 mg, 0.38 mmol), 172 (64 mg, 0.38 mmol) and K2CO3 (160 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 (171) as a solid. 1H NMR 9.12 (s, 1H), 8.49 (q, 1H), 8.36 (s, 1H), 7.87 (t, 1H), 7.56 (q, 1H), 7.21 (s, 2H), 6.11 (s, 2H), 3.13–3.19 (m, 2H), 1.71–1.79 (m, 2H), 1.02 (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-40d91aa7ef964fee997df81efce80ba1
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

Loading…