Citric Acid → 2-(Pyrimidin-5-yl)propan-2-amine

HRID 2294943Notes

Reaction equation

HRID 2294943 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([N:10]=C=O)([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(OCC)(=O)C.C1COCC1>[N:1]1[CH:6]=[C:5]([C:7]([NH2:10])([CH3:9])[CH3:8])[CH:4]=[N:3][CH:2]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 543276785-(2-Isocyanatopropan-2-yl)pyrimidine

Product 1

HCID 450801402-(Pyrimidin-5-yl)propan-2-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude 2-(5-pyrimidinyl)-2-propylisocyanate was treated with a mixture of 1.0N sodium hydroxide (26 mL), water (20 mL) and THF (100 mL) at 0° C. for 30 min, then the mixture was poured into ethyl acetate (200 mL) and water (100 mL). The aqueous layer was acidified to pH 5 with 10% citric acid, extracted twice with ethyl acetate, and then adjusted to pH 11, saturated with sodium chloride, and extracted with methylene chloride (3×250 mL). The combined methylene chloride extracts were dried (Na2SO4) and concentrated in vacuo to give 2-(5-pyrimidinyl)-2-propylamine (950 mg) as a colorless oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. extractionextracted with methylene chloride (3×250 mL)
  3. dry with materialThe combined methylene chloride extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb769b82230d4d6a850f0dd1bb42304a
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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