Triethylamine → 6-chloro-5-fluoro-2-methyl-N-(2-pyridinylmethyl)-4-pyrimidinamine

HRID 1366462Notes

Reaction equation

HRID 1366462 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.C(N(CC)CC)C.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][NH2:25]>C1COCC1.O>[Cl:9][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 866369456-chloro-5-fluoro-2-methyl-N-(2-pyridinylmethyl)-4-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (0.2 g, 1.111 mmol) was dissolved in THF (1 mL). To this solution was added triethylamine (0.17 mL, 1.22 mmol), followed by commercially available (2-pyridinylmethyl)amine (0.11 mL, 1.067 mmol), which was dissolved in THF (1 mL). The reaction was left to stir for 4 hours. The reaction mixture was diluted with water and extracted with ether. The organics were dried (MgSO4) and concentrated to provide 6-chloro-5-fluoro-2-methyl-N-(2-pyridinylmethyl)-4-pyrimidinamine as a yellow wax (0.2517 g, 90%). LCMS: (M+H)+=253.3.

Workup

  1. waitThe reaction was left
  2. extractionextracted with ether
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-487659f0621748b7a1ba11daf299c956
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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