Formaldehyde → (4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanol

HRID 732104Notes

Reaction equation

HRID 732104 reaction equation
[CH:1]1([N:4]2[CH:8]=[N:7][N:6]=[C:5]2[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.[CH2:15]=[O:16]>>[CH:1]1([N:4]2[C:5]([C:9]3[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=3)=[N:6][N:7]=[C:8]2[CH2:15][OH:16])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 578379644-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine

Product 1

HCID 57837966(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanolYield 85%

Conditions

Temperature
135 °C

Procedure

4-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine (6.85 g, 36.8 mmol) was mixed with 37% formaldehyde (30 mL) in a sealed vial and heated at 135° C. o.n. The reaction mixture was concentrated with silica gel and then mixed with MeOH. The mixture was filtered and washed with MeOH. The filtrate was concentrated with silica gel again and loaded on a flash column and eluted with 10% MeOH (2 M NH3) in DCM to give the title compound (6.8 g, 85%). 1H-NMR(DMSO-d6): 8.75(d, 2H), 7.84 (d, 2H), 5.63 (t, 1H), 4.72 (d, 2H), 3.66 (m, 1H), 1.04 (m, 2H), 0.73 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated with silica gel
  2. additionmixed with MeOH
  3. filtrationThe mixture was filtered
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated with silica gel again
  6. washeluted with 10% MeOH (2 M NH3) in DCM

Sources & evidence

ORD record
ord-40f81230b1974b0c987c4fcb16e9b5ff
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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