Ethylamine → Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine

HRID 2266073Notes

Reaction equation

HRID 2266073 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=2[CH:19]([CH3:21])[CH3:20])=[CH:6][N:5]=[C:4]([S:22][CH3:23])[N:3]=1.[CH2:24]([NH2:26])[CH3:25]>>[CH2:24]([NH:26][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=2[CH:19]([CH3:21])[CH3:20])=[CH:6][N:5]=[C:4]([S:22][CH3:23])[N:3]=1)[CH3:25]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 595986204-Chloro-5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidine

Product 1

HCID 59598719Ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amineYield 63%

Conditions

Temperature
50 °C

Procedure

To a glass pressure vessel containing 4-chloro-5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidine (0.212 g, 0.6 mmol) was added 5.0 mL ethyl amine via a cold finger condenser. The vessel was capped and warmed to 50° C. After 16 hours the solution was cooled to room temperature, evaporated and taken up in H2O. The mixture was extracted with ethyl acetate, washed with H2O and then washed with brine. The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo. Purification via flash chromatography (4:1 hexane/ethyl acetate) afforded ethyl-[5-(2-isopropyl-4,5-dimethoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-yl]-amine (0.136 g, 63%) as a white solid.

Workup

  1. customThe vessel was capped
  2. temperatureAfter 16 hours the solution was cooled to room temperature
  3. customevaporated
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with H2O
  6. washwashed with brine
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customPurification via flash chromatography (4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4c11b9bc7650413fa673f1780d7f4b5a
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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