Ethanol → HCID 18982127, compound

HRID 1463270Notes

Reaction equation

HRID 1463270 reaction equation
[NH2:1][C:2]1[C:7]([N:8]=O)=[C:6]([NH2:10])[N:5]=[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:3]=1.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][NH:11][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([NH2:8])=[C:6]([NH2:10])[N:5]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 18982108HCID 18982108, compound

Product 1

HCID 18982127HCID 18982127, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,6-diamino-2-[2-(4-methoxyphenyl)-ethyl]amino-5-nitrosopyrimidine (13.3 g), absolute ethanol (150 ml) and water (150 ml) was heated almost to reflux. Sodium dithionite was added slowly, portionwise until the red colour disappeared. The mixture was filtered hot. After cooling the solid was removed by filtration, triturated with isopropyl alcohol, and dried to give 2-[2-(4-methoxyphenyl)ethyl]amino-4,5,6-triaminopyrimidine as a solid (8.2 g) m.p. 134°-138° C.; NMR: DMSO-d6 ; 2.65-2.85 (t, 2H, CH2 --CH2), 3.25-3.5 (t, 2H, CH2 --NH), 3.7 (s, 3H, OCH3), 6.45-6.65 (b, 2H, NH2), 6.7-6.85 (b, 1H, NH), 6.8-6.9 (d, 2H, aromatic-H), 7.1-7.25 (d, 2H, aromatic-H). Also 2.8-4.0 (v.br, 4H, 2×NH2).

Workup

  1. temperaturewas heated almost
  2. temperatureto reflux
  3. filtrationThe mixture was filtered hot
  4. temperatureAfter cooling the solid
  5. customwas removed by filtration
  6. customtriturated with isopropyl alcohol
  7. customdried

Sources & evidence

ORD record
ord-58dde71edb604443b4dadfbdca11efed
Source dataset
uspto-grants-1994_04
Patent number
US05300509

Reaction notes

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