Water → 5-bromo-N-isopropyl-4-methoxypyrimidin-2-amine

HRID 709971Notes

Reaction equation

HRID 709971 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH:11]([NH2:14])([CH3:13])[CH3:12].O>C1COCC1>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([NH:14][CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 904157805-bromo-N-isopropyl-4-methoxypyrimidin-2-amineYield 634%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-bromo-2-chloro-4-methoxypyrimidine (1.2 g, 5.37 mmol) in THF (20 mL) was treated with TEA (1.57 mL, 10.74 mmol) and isopropylamine (0.7 mL, 8.1 mmol) and heated at 60° C. for 5 h. The mixture was cooled to RT, treated with water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (EtOAc/Hex) to afford 5-bromo-N-isopropyl-4-methoxypyrimidin-2-amine (0.84 g, 634%). 1H NMR (400 MHz, DMSO-d6): δ 8.10 (s, 1H), 7.17 (br s, 1H), 3.96-3.94 (m, 1H), 3.87 (s, 3H), 1.12 (d, J=6.5 Hz, 6H); MS (ESI) m/z: 246.0 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-11aecd4ee10a46dea5a69fd673dea9ac
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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