3-Methoxybenzylamine → HCID 22732345, compound

HRID 1765206Notes

Reaction equation

HRID 1765206 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24]>C(O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:24][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 211563-MethoxybenzylamineHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732345HCID 22732345, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3-methoxybenzylamine (37 μl, 0.290 mmol) in 10 ml of ethanol was stirred at room temperature for 48 h. The mixture was rotary evaporated to dryness and purified by preparative TLC with hexane:ethyl acetate (3:1) to give a yellow solid (14 mg, 20%). 1H NMR (CDCl3): 9.60–9.59 (m, 1H), 8.70–8.66 (m, 2H), 7.40–7.32 (m, 1H), 7.30 (d, J=7.8 Hz, 1H), 6.95 (d, J=7.8 Hz, 1H), 6.91 (s, 1H), 6.85 (dd, J=2.7, 8.4 Hz, 1H), 6.62 (s, 1H), 5.75 (bs, 1H), 4.73 (s, 2H), 3.79 (s, 3H).

Workup

  1. customThe mixture was rotary evaporated to dryness
  2. custompurified by preparative TLC with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b97db858a70f4dacb03253931976b5c1
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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