Ethyl Acetate → 6-chloro-N-(4-methoxybenzyl)-2-methylpyrimidin-4-amine

HRID 1039047Notes

Reaction equation

HRID 1039047 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[OH-].[K+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([CH3:21])[N:15]=1.C(OCC)(=O)C>CN(C=O)C>[Cl:13][C:14]1[N:15]=[C:16]([CH3:21])[N:17]=[C:18]([NH:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 754524-MethoxybenzylamineHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 624837716-chloro-N-(4-methoxybenzyl)-2-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-(4-methoxyphenyl)methanamine (1.51 g, 11 mmol) was added in DMF (15 mL), potassium hydroxide was added and stirred at room temperature for 10 minutes. The reaction was cooled to −2° C., 4,6-dichloro-2-methylpyrimidine (1.63 g, 10 mmol) in DMF (5 mL) was added drop-wise at a speed the internal temperature was controlled <0° C. After 30 minutes, the reaction was added ethyl acetate (50 mL), washed with brine (20 mL×2). The organic phase was dried by magnesium sulfate, filter, concentrated and purified by column chromatography through a 110 gram AnaLogix™ silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow solid.

Workup

  1. temperatureThe reaction was cooled to −2° C.
  2. customwas controlled <0° C
  3. waitAfter 30 minutes
  4. washwashed with brine (20 mL×2)
  5. dry with materialThe organic phase was dried by magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrated
  8. custompurified by column chromatography through a 110 gram AnaLogix™ silica gel cartridge
  9. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e77cadbc1e00400b95919a8603344e5f
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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