Hydrochloric Acid → HCID 178479162, compound

HRID 1586953Notes

Reaction equation

HRID 1586953 reaction equation
C([NH:4][C:5]1[C:6]([OH:13])=[N:7][C:8]([NH2:12])=[N:9][C:10]=1[OH:11])(=O)C.[ClH:14]>>[ClH:14].[NH2:12][C:8]1[N:9]=[C:10]([OH:11])[C:5]([NH2:4])=[C:6]([OH:13])[N:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178474388HCID 178474388, compound

Product 1

HCID 178479162HCID 178479162, compoundYield 46%

Procedure

5-Acetamido-2-amino-4,6-dihydroxypyrimidine (700 g crude) (ex. guanidinium carbonate, diethyl acetamido malonate and ethanol refluxed 48 hours), concentrated hydrochloric acid (2 liters water), (200 ml), were heated to 70° and kept at 70°-75° for 1 hour, then cooled in an ice bath. The product was filtered, washed with HCl (80 ml conc HCl in water 170 ml), then acetone (1 liter), and air dried at 40° to give the title compound (344.5 g). Found: C 24.53, H 4.33, N 28.9 Cl 17.9; C4H6N4O2 ·HCl·H2O requires C 24.4, H 4.6, N 28.5, Cl 18.0%. NMR C13 84.59, 115.24, 157.22 ppm DMSO MS/FAB M+H 143. Vacuum oven drying at 0.5 mm and 85° C. with argon protection gave 320 g (46% yield).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe product was filtered
  3. washwashed with HCl (80 ml conc HCl in water 170 ml)
  4. dry with materialacetone (1 liter), and air dried at 40°

Sources & evidence

ORD record
ord-4646bac3659545ceb04d4bd4bfff42bc
Source dataset
uspto-grants-1993_06
Patent number
US05216161

Reaction notes

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