Ethanol → 6-Chloro-4-ethoxypyrido[3,2-d]pyrimidin-2-amine

HRID 1517457Notes

Reaction equation

HRID 1517457 reaction equation
Cl[C:2]1[C:3]2[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:4]=2[N:5]=[C:6]([NH:8]C(=O)C)[N:7]=1.[CH2:17]([OH:19])[CH3:18]>C(OCC)(=O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:4]2[N:5]=[C:6]([NH2:8])[N:7]=[C:2]([O:19][CH2:17][CH3:18])[C:3]=2[N:15]=1

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 57698319N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamide

Product 1

HCID 597672176-Chloro-4-ethoxypyrido[3,2-d]pyrimidin-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-(4,6-dichloro-pyrido[3,2-d]pyrimidin-2-yl)-acetamide (0.98 g, 3.8 mmol) in ethanol (35 mL) was added a solution of 21% Na ethanolate in ethanol (2.8 mL, 7.6 mmol). After stirring at room temperature for one hour, the solution was diluted with ethyl acetate then washed with brine. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated to yield the pure title compound as a beige solid (0.6 g, yield 70%) which was characterised as follows: MS (m/z) 225.6 [M+H]+.

Workup

  1. washthen washed with brine
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eba556e9c5534d8b92a61d9725eed185
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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