tert-Butyl methyl ether → Pyrazine-2-carboxamidine hydrochloride

HRID 1783447Notes

Reaction equation

HRID 1783447 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)#[N:5].[Cl-:12].[NH4+:13].C(OC)(C)(C)C>CO>[ClH:12].[N:7]1[CH:8]=[CH:9][N:10]=[CH:11][C:6]=1[C:4]([NH2:13])=[NH:5]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 73172PyrazinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 470895Pyrazine-2-carboxamidine hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of sodium methoxide (NaOCH3) (51.4 g, 0.952 mol) in methanol (3800 ml) there is added cyanopyrazine (1.00 KG, 9.53 mol) slowly at room temperature. The mixture is heated to 30° C. and stirred for 6 h. The mixture is cooled to 25° C. followed by the addition of ammonium chloride (NH4Cl) (572 g, 10.5 mol). The reaction mixture is stirred for 22 h and methyl t-butyl ether (4000 mL) is added and the mixture is stirred for 15 min forming a solid. The solid is filtered and washed with methyl t-butyl ether (2×1000 mL) then dried at 40° C./0-10 mmHg for 17 h to give white solid product (1435 g) in 95% yield with 95% HPLC purity. 1H NMR (DMSO-D6): δ 9.7 (bs, 3H), 9.49 (d, 1H, J=1.5 Hz), 9.04 (m, 1H), 8.93 (t, 1H, J=1.5 Hz)

Workup

  1. temperatureThe mixture is cooled to 25° C.
  2. stirringThe reaction mixture is stirred for 22 h
  3. stirringthe mixture is stirred for 15 min
  4. customforming a solid
  5. filtrationThe solid is filtered
  6. washwashed with methyl t-butyl ether (2×1000 mL)
  7. customthen dried at 40° C./0-10 mmHg for 17 h

Sources & evidence

ORD record
ord-a8b98767deda4894a482860eed95169e
Source dataset
uspto-grants-2009_03
Patent number
US07501423B2

Reaction notes

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