Isobutylamine → HCID 89876049, compound

HRID 594119Notes

Reaction equation

HRID 594119 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.C(N(CC)CC)C.[CH2:19]([NH2:23])[CH:20]([CH3:22])[CH3:21]>>[CH3:21][CH:20]([CH3:22])[CH2:19][NH:23][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1

Participants

4

Reactant 3

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidine

Product 1

HCID 89876049HCID 89876049, compound

Procedure

A mixture of 4-chloro-2-(trifluoromethyl)pyrimidine (548 mg, 3 mmol) and triethylamine (0.460 mL, 3.30 mmol) in isobutylamine (1.5 mL) was stirred at room temperature for 11 hours and 30 minutes (Care: exotherm). The mixture was evaporated, then dichloromethane (DCM) (5 mL) and water (5 mL) added. The organic layer was separated and purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient). The relevant fractions were combined and concentrated to yield the title compound, 548 mg. LCMS (2 min, formic) Rt 1.08 min, m/z (ES+) 220 (M+H).

Workup

  1. customThe mixture was evaporated
  2. additiondichloromethane (DCM) (5 mL) and water (5 mL) added
  3. customThe organic layer was separated
  4. custompurified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15939fe87aa24e61967d2c2a70fe38a9
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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