Hydrochloric Acid → Methyl 5-(hydroxymethyl)pyrazine-2-carboxylate

HRID 1429626Notes

Reaction equation

HRID 1429626 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+].CO.Cl>C1COCC1.[Cl-].[Na+].O>[OH:2][CH2:1][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 44515461Methyl 5-formylpyrazine-2-carboxylate

Product 1

HCID 66869530Methyl 5-(hydroxymethyl)pyrazine-2-carboxylateYield 52.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 5-formylpyrazine-2-carboxylate (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.07 (s, 3 H), 4.98 (br. s., 2 H), 8.80 (s, 1 H), 9.27 (s, 1 H)

Workup

  1. stirringThe reaction mixture was stirred for a further 20 mins
  2. extractionThe mixture was extracted with EtOAc (3×40 mL)
  3. dry with materialthe combined organic portions dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-fe3b7cf4278f4aceafc576cede268b99
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

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