Hydrochloric Acid → HCID 178430736, compound

HRID 1680201Notes

Reaction equation

HRID 1680201 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13]2[NH:18][C:17]([CH3:20])([CH3:19])[N:16]=[C:15]([O:21]CC)[N:14]=2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.C[Si](I)(C)C.Cl>S1(CCCC1)(=O)=O>[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13]2[NH:18][C:17]([CH3:19])([CH3:20])[N:16]=[C:15]([OH:21])[N:14]=2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 178467423HCID 178467423, compound

Product 1

HCID 178430736HCID 178430736, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-ethoxy-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide (0.55 g., 0.0016 mole) in sulfolane (10 ml.) is added trimethylsilyl iodide (1.5 ml.). The reaction mixture is stirred for 5 hours at 45° C., poured into ice water (30 ml.) containing hydrochloric acid (1.5 ml.), then extracted with chloroform (2×15 ml.) The aqueous layer is made basic with ammonia to give 420 mg. of 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-hydroxy-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide which melts at 266°-8° C. after reprecipitation from dilute hydrochloric acid with ammonia.

Workup

  1. extractionextracted with chloroform (2×15 ml.) The aqueous layer
  2. customto give 420 mg
  3. customof 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-hydroxy-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide which melts at 266°-8° C. after reprecipitation from dilute hydrochloric acid with ammonia

Sources & evidence

ORD record
ord-3feb3f03fe62481298d8160d446f0fe2
Source dataset
uspto-grants-1981_06
Patent number
US04272537

Reaction notes

Loading…