6-Azido-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine → 6-Amino-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

HRID 965691Notes

Reaction equation

HRID 965691 reaction equation
[N:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=2)[C:5]=1[CH2:23][CH2:24][CH3:25])=[N+]=[N-]>CO.[Pd]>[F:22][C:18]1[N:17]=[C:16]([C:12]2[N:11]([CH2:10][C:6]3[N:7]=[CH:8][N:9]=[C:4]([NH2:1])[C:5]=3[CH2:23][CH2:24][CH3:25])[CH:15]=[CH:14][N:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 223131686-Azido-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Product 1

HCID 117230296-Amino-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 10 mg) is added to a solution of 6-azido-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (2 mmol) in MeOH (20 mL). The mixture is stirred under H2 at 30 psi for 4 hours. The catalyst is filtered away and the filtrate is evaporated in vacuo to give the title compound as a yellow solid. 1H NMR (CDCl3) 8.35 (s, 1H), 8.12-8.14 (m, 1H), 7.82 (t, 1H), 7.17 (d, 1H), 7.13 (d, 1H), 6.80-6.82 (m, 1H), 5.92 (s, 2H), 4.88 (s, 2H), 2.53-2.57 (m, 2H), 1.48-1.55 (m, 2H), 0.95 (t, 3H).

Workup

  1. filtrationThe catalyst is filtered away
  2. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-98d88fe2fb9045a3b3ff9c2065ad4379
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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