2-Cyanopyrimidine → HCID 178451828, compound

HRID 605020Notes

Reaction equation

HRID 605020 reaction equation
[NH:1]([C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O)[NH2:2].[C:18]([C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1)#[N:19]>C(O)CCC>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[C:18]1[NH:2][N:1]=[C:3]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[N:19]=1

Participants

4

Reactant 2

HCID 27579792-CyanopyrimidineHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 178451828HCID 178451828, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (10.1 g, 41.5 mmol) and 2-cyanopyrimidine (4.36 g, 41.5 mmol) in 1-butanol (20 mL) was heated to reflux for 48 hours. The mixture was concentrated, suspended in ether, and filtered to give tert-butyl 4-(5-pyrimidin-2-yl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate as a solid. MS (M+H+): 331.2 observed; 1H-NMR (400 MHz, CD3OD): δ 8.92 (d, J=4.0 Hz, 2H), 7.52 (t, J=4.0 Hz, 1H), 4.18-4.15 (m, 2H), 3.14-3.08 (m, 1H), 2.98 (br.s, 2H), 2.07-2.01 (m, 2H), 1.85-1.77 (m, 2H), 1.48 (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. concentrationThe mixture was concentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d15832fd59004507812525645a34505b
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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