Formic Acid → 2-(5-aminopyrazin-2-yl)propan-2-ol

HRID 2192915Notes

Reaction equation

HRID 2192915 reaction equation
C(O)=O.C(N)CCC.[OH:9][C:10]([C:13]1[N:14]=[CH:15][C:16]([NH:19]C(=O)OCC=C)=[N:17][CH:18]=1)([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>C1COCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:19][C:16]1[N:17]=[CH:18][C:13]([C:10]([OH:9])([CH3:11])[CH3:12])=[N:14][CH:15]=1

Participants

9

Reactant 4

HCID 284Formic AcidHCID 8007ButylamineHCID 516892Sodium BicarbonateHCID 59570955HCID 59570955, compound

Product 1

HCID 595710662-(5-aminopyrazin-2-yl)propan-2-olYield 64.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of formic acid (48 mg) and n-butylamine (76 mg) in THF (10 mL) was added tetrakistriphenylphosphinepalladium (30 mg) and allyl [5-(1-hydroxy-1-methylethyl)pyrazin-2-yl]carbamate (123 mg) at room temperature, followed by stirring at room temperature for 5 hours. To the reaction mixture was added water, saturated aqueous sodium bicarbonate, and saturated brine at room temperature, followed by extraction with a solvent (chloroform:isopropyl alcohol=4:1). The organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by concentration was purified by a thin layer silica gel chromatography (chloroform:methanol=10:1) to obtain 2-(5-aminopyrazin-2-yl)propan-2-ol (51 mg) as a pale yellow oily substance.

Workup

  1. extractionfollowed by extraction with a solvent (chloroform:isopropyl alcohol=4:1)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by a thin layer silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-d67ca7b5cde64cb1aec1fc2aa93fb31b
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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