Triethylamine → HCID 86675236, compound

HRID 2370060Notes

Reaction equation

HRID 2370060 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[CH3:11][S:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C>C(O)(C)C>[Cl:9][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:15][CH2:14][CH2:13][S:12][CH3:11])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87697(2-(Methylthio)ethyl)amineHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Product 1

HCID 86675236HCID 86675236, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Heat a solution of 4,6-dichloro-2-methyl-pyrimidin-5-amine (46.0 g, 0.258 mol), 2-(methylthio)ethyl amine (40.05 g, 0.439 mol) and triethylamine (53.3 g, 0.517 mol) in isopropanol (500 mL) at 90° C. for 30 h. Cool the reaction mixture to room temperature and concentrate. Dissolve the residue in dichloromethane (2 L) and wash with water (2×500 mL) and brine (500 mL). Dry the organic layer over solid sodium sulfate, filter, and evaporate to afford a brown solid. Purify the residue on a silica gel column eluting with ethyl acetate to give the title compound (56 g). ES/MS (m/z) 233 (M+1).

Workup

  1. concentrationconcentrate
  2. dissolutionDissolve the residue in dichloromethane (2 L)
  3. washwash with water (2×500 mL) and brine (500 mL)
  4. dry with materialDry the organic layer over solid sodium sulfate
  5. filtrationfilter
  6. customevaporate
  7. customto afford a brown solid
  8. customPurify the residue on a silica gel column
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0c1e504901364183a0c586fbf70203dd
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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