Sodium Hydroxide → 3,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide
Reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH3:8][S:9][C:10](=[NH:12])[NH2:11].[NH2:13][C:14]1[C:15]([C:22](OC(C)=CC(=O)NC(C)(C)C)=[O:23])=[N:16][C:17]([Cl:21])=[C:18]([NH2:20])[N:19]=1>C(Cl)Cl.O1CCCC1>[NH2:13][C:14]1[C:15]([C:22]([NH:12][C:10]([S:9][CH3:8])=[NH:11])=[O:23])=[N:16][C:17]([Cl:21])=[C:18]([NH2:20])[N:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To NaOH (1 M in water; 18.7 mL; 18.7 mmol) is added S-methylisothiourea sulphate (4.25 g; 15.3 mmol). The mixture is stirred until complete dissolution is achieved. CH2Cl2: tetrahydrofuran (1:1; 30 mL) and then 1-(tert-butylcarbamoyl)prop-1-en-2-yl 3,5-diamino-6-chloropyrazine-2-carboxylate (Intermediate 2; 2.00 g; 6.10 mmol) are added and the mixture is stirred at room temperature over night. The organic solvents are evaporated, then water (50 mL) is added. The precipitate formed is collected by filtration while applying suction, washed successively with water, methanol and then with diethyl ether and then dried at 50° C. to yield the title compound (1.33 g, 84% of theory).
Workup
- stirringthe mixture is stirred at room temperature over night
- customThe organic solvents are evaporated
- additionwater (50 mL) is added
- customThe precipitate formed
- filtrationis collected by filtration
- washwashed successively with water, methanol
- dry with materialwith diethyl ether and then dried at 50° C.
Sources & evidence
- ORD record
- ord-b41ee49f7d3f408aa8230a553ece134d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841309B2
Reaction notes
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