Triethylamine → 2-Chloro-5-(chloromethyl)-N-(2,2-dimethylpropyl)pyrimidin-4-amine

HRID 2216277Notes

Reaction equation

HRID 2216277 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][Cl:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:18][C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH3:18])[C:5]([CH2:9][Cl:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79882NeopentylamineHCID 135682792,4-Dichloro-5-(chloromethyl)pyrimidine

Product 1

HCID 219418692-Chloro-5-(chloromethyl)-N-(2,2-dimethylpropyl)pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 3.47 g (17.57 mmol) of 2,4-dichloro-5-choromethyl-pyrimidine and 2.9 ml (21.08 mmol) triethylamine in 29 ml of THF is cooled to −5° C. and 2.2 ml (17.57 mmol) 2,2-dimethyl-propylamin is added over a period of 15 minutes. The reaction mixture is stirred at −5° C. for additional 2 h, then diluted with ethyl acetate and extracted once with brine. The organic layer is separated and dried over Na2SO4. Purification of the crude product by flash chromatography (hexanes/ethyl acetate) yields (2-chloro-5-chloromethyl-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine as white crystalls.

Workup

  1. extractionextracted once with brine
  2. customThe organic layer is separated
  3. dry with materialdried over Na2SO4
  4. customPurification of the crude product by flash chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-b3819ba2f485480681881971f8c97bb9
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

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