2-Methoxyethylamine → HCID 89814334, compound

HRID 522715Notes

Reaction equation

HRID 522715 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:10]=[N:9][C:8](SC)=[N:7][C:6]=2[N:13]=1.[CH3:14][O:15][CH2:16][CH2:17][NH2:18]>CCOC(C)=O>[CH3:14][O:15][CH2:16][CH2:17][NH:18][C:8]1[N:9]=[CH:10][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[N:13][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 866970117-Methyl-2-(methylthio)pyrido[2,3-d]pyrimidine

Product 1

HCID 89814334HCID 89814334, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Heat a solution of 7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidine (2.6 g, 13.6 mmol) and 2-methoxyethanamine (6 mL) with microwave irradiation at 180° C. for 2 h. Cool the mixture to RT, dissolve in EtOAc, wash with water, then brine, dry over Na2SO4 and concentrate under reduced pressure to give N-(2-methoxyethyl)-7-methylpyrido[2,3-d]pyrimidin-2-amine (2.7 g, 91%). Treat a solution of N-(2-methoxyethyl)-7-methylpyrido[2,3-d]pyrimidin-2-amine (2.35 g, 10.7 mmol) in THF (100 mL) portion wise with NBS (1.8 g, 10.7 mmol) and stir at RT for 2 h. Concentrate the reaction mixture to dryness, dissolve in EtOAc, wash with water, then brine, dry the organics over Na2SO4, concentrate and purify by HPLC to afford the title compound (0.55 g, 26%). MS (m/z): 297.0 (M+1+).

Workup

  1. customwith microwave irradiation at 180° C. for 2 h
  2. washwash with water
  3. dry with materialbrine, dry over Na2SO4
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b5f03eae0a404b669a25a270f56f0010
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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