Water → 2-(2-Propoxyphenyl)pteridin-4(3H)-one

HRID 728015Notes

Reaction equation

HRID 728015 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[N:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][CH3:24])[NH:10][C:11](=[O:14])[C:12]=1[NH2:13].O.[CH:26]([CH:28]=O)=O.O>C(O)CCC>[CH2:22]([O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:9]1[NH:10][C:11](=[O:14])[C:12]2[C:7](=[N:6][CH:26]=[CH:28][N:13]=2)[N:8]=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 21880647Glyoxal hydrateHCID 1363645694,5-Diamino-2-(propoxyphenyl)pyrimidin-6-one sulphate

Product 1

HCID 1356707932-(2-Propoxyphenyl)pteridin-4(3H)-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred mixture of 4,5-diamino-2-(2-propoxyphenyl)pyrimidin-6-one sulphate (1.25 g), glyoxal hydrate (0.4 g), water (62.5 ml) and n-butanol (1 ml) was heated under reflux for one hour to afford a crude product (0.97 g) which was collected and washed with water. The crude product together with another sample (0.12 g) similarly prepared was eluted from a silica column with chloroform. The combined fractions containing product were evaporated under reduced pressure to afford a solid (0.96 g) which was recrystallised from ethanol-water to afford the title compound, 0.8 g, m.p. 177.5°-178.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. customto afford a crude product (0.97 g) which
  4. customwas collected
  5. washwashed with water
  6. customThe crude product together with another sample (0.12 g) similarly prepared
  7. washwas eluted from a silica column with chloroform
  8. additionThe combined fractions containing product
  9. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-f9e6ff7c12aa4c839f0a1ba829d0207b
Source dataset
uspto-grants-1991_09
Patent number
US05047404

Reaction notes

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