Ammonia → HCID 59598538, compound

HRID 81793Notes

Reaction equation

HRID 81793 reaction equation
[NH3:1].Cl[C:3]1[C:8]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])=[CH:7][N:6]=[C:5]([S:22][CH3:23])[N:4]=1>CCO>[Cl:16][C:14]1[C:13]([O:17][CH3:18])=[CH:12][C:11]([CH:19]([CH3:21])[CH3:20])=[C:10]([CH:15]=1)[CH2:9][C:8]1[C:3]([NH2:1])=[N:4][C:5]([S:22][CH3:23])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 595986914-Chloro-5-(5-chloro-2-isopropyl-4-methoxy-benzyl)-2-methylsulfanyl-pyrimidine

Product 1

HCID 59598538HCID 59598538, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To 25 ml of saturated NH3 in EtOH was added 4-Chloro-5-(5-chloro-2-isopropyl-4-methoxy-benzyl)-2-methylsulfanyl-pyrimidine (0.580 g, 1.6 mmol). The solution was warmed to 85° C. in a sealed reaction vessel. After 3 days the solution was cooled, concentrated in vacuo and suspended in CH2Cl2. The precipitate was filtered and the mother liquor was concentrated in vacuo. Purification via flash chromatography (7:3 hexane/ethyl acetate) afforded 5-(5-chloro-2-isopropyl-4-methoxy-benzyl)-2-methylsulfanyl-pyrimidin-4-ylamine (0.504 g, 92%) as a white solid.

Workup

  1. temperatureAfter 3 days the solution was cooled
  2. concentrationconcentrated in vacuo
  3. filtrationThe precipitate was filtered
  4. concentrationthe mother liquor was concentrated in vacuo
  5. customPurification via flash chromatography (7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d5383fdd0aec4745ba996e789f22a227
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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