Benzaldehyde → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 916651Notes

Reaction equation

HRID 916651 reaction equation
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][NH2:21])[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.BrBr.[CH3:35]CO>>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:35][N:20]4[N:21]=[C:18]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[N:17]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 24408BromineHCID 57503304{6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine

Product 1

HCID 113045167-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Procedure

A mixture of {6-[2-(3,-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine (131) (60 mg, 0.18 mmol), benzaldehyde (21 mg, 0.2 mmol) in EtOH is refluxed for 4 hours. Solvent is removed in vacuo. HOAc (2 mL) is added to the residue, and then bromine (0.3 mmol) is slowly added. The mixture is stirred at room temperature overnight. Solvent is removed in vacuo and the residue is treated with NaHCO3 (aq) and DCM. The organic layer is separated and the aqueous layer is extracted with DCM (2×0 mL). The combined organic layers are dried (MgSO4), the solvent is removed, and the crude purified by PTLC (10% MeOH in DCM) to give a white solid; 1H-NMR (CDCl3) δ: 8.93 (s, 1H), 8.44 (dd, 1H), 7.78–7.88 (m, 2H), 7.51–7.63 (m, 4H), 7.22–7.36 (m, 3H), 5.82 (s, 2H), 3.05 (q, 2H), 1.70–1.80 (m, 2H), 1.02 (t, 3H).

Workup

  1. temperatureis refluxed for 4 hours
  2. customSolvent is removed in vacuo
  3. additionHOAc (2 mL) is added to the residue
  4. customSolvent is removed in vacuo
  5. additionthe residue is treated with NaHCO3 (aq) and DCM
  6. customThe organic layer is separated
  7. extractionthe aqueous layer is extracted with DCM (2×0 mL)
  8. dry with materialThe combined organic layers are dried (MgSO4)
  9. customthe solvent is removed
  10. customthe crude purified by PTLC (10% MeOH in DCM)
  11. customto give a white solid

Sources & evidence

ORD record
ord-ce530d4ec1374af4987022e6a833c09d
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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