Ethylamine → Ethyl-{6-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-amine

HRID 965693Notes

Reaction equation

HRID 965693 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[C:3]=1[CH2:21][CH2:22][CH3:23].[CH2:24]([NH2:26])[CH3:25]>>[CH2:24]([NH:26][C:2]1[C:3]([CH2:21][CH2:22][CH3:23])=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[N:5]=[CH:6][N:7]=1)[CH3:25]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 223131636-Chloro-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Product 1

HCID 10359910Ethyl-{6-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-amine

Conditions

Temperature
70 °C

Procedure

A mixture of 6-chloro-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (60 mg, 0.18 mmol) and ethylamine (2M in THF, 2 mL) is heated at 70° C. in a sealed tube overnight. Solvent is removed. Water (10 mL) and ethyl acetate (15 mL) are added. The layers are separated—the aqueous layer is extracted with ethyl acetate (2×20 mL) and the organic layers are combined. On drying, the solvent is removed in vacuo. Preparative TLC separation gives the title compound. LC-MS (M+1) 341.2 (retention time: 1.00 min).

Workup

  1. customSolvent is removed
  2. additionWater (10 mL) and ethyl acetate (15 mL) are added
  3. extractionis extracted with ethyl acetate (2×20 mL)
  4. customOn drying
  5. customthe solvent is removed in vacuo
  6. customPreparative TLC separation

Sources & evidence

ORD record
ord-f898fce0b597421986e07d152fff10d0
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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