Water → HCID 59446979, compound

HRID 1946665Notes

Reaction equation

HRID 1946665 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[CH3:13][NH:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH3:13])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 59446979HCID 59446979, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, OR2558, 25.00 g; 120 mmol) in THF (500 mL) was treated with a solution of n-methylcyclohexylamine (Aldrich, 15.7 ml; 121 mmol) and triethylamine (18.4 ml; 133 mmol) in THF (250 mL). The reaction mixture was stirred for 16 hours at RT. Water (250 mL) was poured into the reaction mixture which was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to obtain the crude product, which was purified by recrystallisation from MTBE. The title product was obtained as a beige solid (25.7 g, 75%).

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain the crude product, which
  6. customwas purified by recrystallisation from MTBE

Sources & evidence

ORD record
ord-d9bc4d9810c44dfbb90ec39aaafa77a7
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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