4,6-Dichloropyrimidine → HCID 55190931, compound

HRID 1619713Notes

Reaction equation

HRID 1619713 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].[Cl:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[CH:25][N:24]=1>C(O)CCC>[Cl:22][C:23]1[N:24]=[CH:25][N:26]=[C:27]([NH:15][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:12]=2[O:11][CH3:10])[CH:28]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 55190931HCID 55190931, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Diisopropylethylamine (8.10 mL, 46.50 mmol) and 2,4-dimethoxybenzylamine (2.52 mL, 16.78 mmol) were added to a solution of 4,6-dichloropyrimidine (2.50 g, 16.78 mmol) in butanol (80 mL) and reaction mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled to room temperature and washed with water (30 mL). The aqueous layer was extracted with ethyl acetate (30 mL) and the combined organic layers were dried over anhydrous MgSO4, filtered and evaporated. The residue was triturated in heptane to give the title compound (4.00 g, 85%) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (30 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (30 mL)
  4. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated in heptane

Sources & evidence

ORD record
ord-d7a1a4d471a049beb5a2b3f1606343e2
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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