Ethanol → HCID 58466487, compound

HRID 2092266Notes

Reaction equation

HRID 2092266 reaction equation
[Br:1][C:2]1[C:15](=[O:16])[N:14]([CH3:17])[C:5]2[N:6]=[C:7](S(C)(=O)=O)[N:8]=[CH:9][C:4]=2[CH:3]=1.[CH3:18][NH2:19].C(O)C>CC(O)C>[Br:1][C:2]1[C:15](=[O:16])[N:14]([CH3:17])[C:5]2[N:6]=[C:7]([NH:19][CH3:18])[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 58466452HCID 58466452, compound

Product 1

HCID 58466487HCID 58466487, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Charged a flask with 6-bromo-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.910 g, 2.86 mmol, prepared by reference in Scheme 6E) and 10.0 mL IPA. Chilled suspension to 0° C. and treated with methylamine 33% wt. solution in ethanol (1.78 ml, 14.3 mmol). After addition was complete, the bath was removed and the reaction mixture was allowed to warm to ambient temperature and stirred overnight. The crude reaction mixture was filtered and washed with ethanol (2×30 mL) and air-diced to afford a white microcrystalline solid: 6-bromo-8-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (0.637 g, 82.8% yield). MS (M+H)+ 269, 271.

Workup

  1. additionAfter addition
  2. customthe bath was removed
  3. temperatureto warm to ambient temperature
  4. customThe crude reaction mixture
  5. filtrationwas filtered
  6. washwashed with ethanol (2×30 mL) and air-diced
  7. customto afford a white microcrystalline solid

Sources & evidence

ORD record
ord-1baf80b259ee40679b1df1bec934ba8c
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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