N-bromobutanimide → 6-Bromo-N-(2-methoxyethyl)-7-methylpyrido[2,3-d]pyrimidin-2-amine

HRID 522716Notes

Reaction equation

HRID 522716 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[N:7]=[CH:8][C:9]2[CH:15]=[CH:14][C:13]([CH3:16])=[N:12][C:10]=2[N:11]=1.C1C(=O)N([Br:24])C(=O)C1>C1COCC1>[Br:24][C:14]1[C:13]([CH3:16])=[N:12][C:10]2[N:11]=[C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[N:7]=[CH:8][C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89814334HCID 89814334, compound

Product 1

HCID 898141436-Bromo-N-(2-methoxyethyl)-7-methylpyrido[2,3-d]pyrimidin-2-amineYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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. concentrationConcentrate the reaction mixture to dryness
  2. dissolutiondissolve in EtOAc
  3. washwash with water
  4. dry with materialbrine, dry the organics over Na2SO4
  5. concentrationconcentrate
  6. custompurify by HPLC

Sources & evidence

ORD record
ord-03d248653b0c4788a3213dcd10196e13
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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