Sodium Hydroxide → methyl N-(3,5-diamino-6-bromopyrazine-2-carbonyl)carbamimidothioate

HRID 408642

Reaction equation

HRID 408642 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)(CC)C)=[O:34])=[N:27][C:28]([Br: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]([Br:32])=[C:29]([NH2:31])[N:30]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 22492792Mtbe thfHCID 866824751-(2-Methyl-2-butyl-carbamoyl)prop-1-en-2-yl 3,5-diamino-6-bromopyrazine-2-carboxylate

Product 1

HCID 140606262methyl N-(3,5-diamino-6-bromopyrazine-2-carbonyl)carbamimidothioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To NaOH (1 mol/l in water; 30 mL; 30 mmol) is added S-methylisothiourea sulfate (5.42 g; 19.5 mmol. The mixture is stirred until complete solution is achieved. TBME/THF (1:1; 100 mL) and then 1-(2-methyl-2-butyl-carbamoyl)prop-1-en-2-yl 3,5-diamino-6-bromopyrazine-2-carboxylate (Intermediate B.62; 7.52 g; 19.5 mmol) are added and the mixture is stirred at r.t. over night, then water (100 mL) is added. The precipitate formed is filtered off with suction, washed with THF/water (1:2) 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 with THF/water (1:2)
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-f0162b53601240d58aebe7c019b08b19
Source dataset
uspto-grants-2014_06
Patent number
US08759349B2

Linked notes

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