Sodium Hydroxide → 3,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide

HRID 1522906Notes

Reaction equation

HRID 1522906 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH3:8][S:9][C:10](=[NH:12])[NH2:11].CC(OC)(C)C.C1COCC1.[NH2:24][C:25]1[C:26]([C:33](OC(C)=CC(=O)NC(C)(C)C)=[O:34])=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1>O>[NH2:24][C:25]1[C:26]([C:33]([NH:12][C:10]([S:9][CH3:8])=[NH:11])=[O:34])=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 22492792Mtbe thfHCID 540167941-(Tert-butylcarbamoyl)prop-1-en-2-yl 3,5-diamino-6-chloropyrazine-2-carboxylate2×

Product 1

HCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To NaOH (1 mol/l in water; 9.2 mL; 9.2 mmol) is added S-methylisothiourea sulphate (1.78 g; 6.1 mmol. The mixture is stirred until complete solution is achieved. TBME/THF (1:1; 30 mL) and then 1-(tert-butylcarbamoyl)prop-1-en-2-yl 3,5-diamino-6-chloropyrazine-2-carboxylate (Intermediate B; 2.00 g; 6.10 mmol) are added and the mixture is stirred at r.t. over night, then water (6 mL) is added. The precipitate formed is filtered off with suction, washed successively with water, methanol and then with diethyl ether and then dried at 50° C. to yield the title compound.

Workup

  1. stirringthe mixture is stirred at r.t. over night
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. washwashed successively with water, methanol
  5. dry with materialwith diethyl ether and then dried at 50° C.

Sources & evidence

ORD record
ord-1bec9929c97e41ea9085609d4924a9c0
Source dataset
uspto-grants-2015_07
Patent number
US09078909B2

Reaction notes

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