Acetic Acid → HCID 23310600, compound

HRID 746209Notes

Reaction equation

HRID 746209 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:14][CH3:15].[NH2:16][C:17]1[N:22]=[C:21]([NH2:23])[C:20]([CH2:24]O)=[CH:19][N:18]=1.C(O)(=O)C.[ClH:30]>CC(C)=O>[ClH:30].[ClH:30].[NH2:16][C:17]1[N:22]=[C:21]([NH2:23])[C:20]([CH2:24][C:5]2[C:6]3[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=3)[C:2]([NH2:1])=[C:3]([O:14][CH3:15])[CH:4]=2)=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 2958782,4-Diamino-5-pyrimidinemethanolHCID 233106032,7-Dimethoxy-1-naphthalenamine

Product 1

HCID 23310600HCID 23310600, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-amino-2,7-dimethoxynaphthalene (2.03 g, 10.00 mmol) [O. Fischer and W. Kern, J. Prakt. Chem., 94, 34(1916)], 2,4-diamino-5-hydroxymethylpyrimidine (1.40 g, 10.0 mmol), glacial acetic acid (20 mL) and concentrated hydrochloric acid (1.4 mL) was refluxed for 2 hr. The cooled reaction mixture was diluted with acetone and the resulting precipitate was collected and dried giving the title compound as a grey solid (3.40 g, 78%). Recrystallization from aqueous ethanol with concentrated HCl gave an analytical sample, mp >210° dec. Anal. Calcd for C17H19N5O2.2HCl.2H2O: C, 47.01; H, 5.80; N, 16.12; Cl, 16.32. Found: C, 47.19; H, 5.90; N, 16.05; Cl, 16.37.

Workup

  1. customThe cooled reaction mixture
  2. customthe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-01b0ecb9947b403a89b7be39ba689d17
Source dataset
uspto-grants-1986_07
Patent number
US04603136

Reaction notes

Loading…