Dimethylamine → HCID 86208394, compound

HRID 1352885Notes

Reaction equation

HRID 1352885 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1>O1CCCC1.C(N(CC)C(C)C)(C)C>[Cl:11][C:9]1[N:8]=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=[C:5]([N:2]([CH3:3])[CH3:1])[CH:10]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 6171324,6-Dichloro-N-phenyl-2-pyrimidinamine

Product 1

HCID 86208394HCID 86208394, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

Dimethylamine in tetrahydrofuran (2M, 15 mL) was added to a solution of 4,6-dichloro-N-phenyl-2-pyrimidinamine (0.715 g, 2.97 mmol) in tetrahydrofuran (30 mL) and N,N-diisopropylethylamine (0.52 mL). The resulting mixture was stirred at room temperature overnight. The solvent was removed and the crude material was purified by flash chromatography on silica gel, eluting with ethyl acetate/hexane (1:9). The eluent was removed, giving 6-chloro-N4,N4-dimethyl-N2-phenyl-2,4-pyrimidinediamine (0.592 g, 2.39 mmol, 80%, Rf=0.3).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by flash chromatography on silica gel
  3. washeluting with ethyl acetate/hexane (1:9)
  4. customThe eluent was removed

Sources & evidence

ORD record
ord-7399d8e37d224017bc4715f62d2eb7a2
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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