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

HRID 408641

Reaction equation

HRID 408641 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-carboxylate

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 sulfate (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.61; 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-2961d83e8d644394865d8db588fc6d4d
Source dataset
uspto-grants-2014_06
Patent number
US08759349B2

Linked notes

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