Water → HCID 86691693, compound

HRID 522266

Reaction equation

HRID 522266 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[Cl:10][C:11]1[N:16]=[C:15]([Cl:17])[C:14]([N+:18]([O-:20])=[O:19])=[C:13](Cl)[N:12]=1.O>C1COCC1.CCOC(C)=O>[Cl:10][C:11]1[N:12]=[C:13]([NH:5][CH3:3])[C:14]([N+:18]([O-:20])=[O:19])=[C:15]([Cl:17])[N:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8471TriethylamineHCID 42978432,4,6-Trichloro-5-nitropyrimidine

Product 1

HCID 86691693HCID 86691693, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 2 M solution of methylamine and triethylamine (1.8 mL) in THF (4.6 mL) were added to a solution of 2,4,6-trichloro-5-nitropyrimidine (2 g) in THF (30 mL) under ice-cooling, and the mixture was stirred for 1 hour under ice-cooling. After water was added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=99:1 to 90:10), whereby 2,6-dichloro-N-methyl-5-nitropyrimidine-4-amine (680 mg) was obtained as a pale yellow solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washthe extract was washed with water and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=99:1 to 90:10)

Sources & evidence

ORD record
ord-eafeb1729d4047ca972518043fa6f237
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Linked notes

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