(R)-3-(2-Cyclopropyl-5-nitro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester → (R)-3-(5-Amino-2-cyclopropyl-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175202Notes

Reaction equation

HRID 2175202 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([CH:23]2[CH2:25][CH2:24]2)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][N:17]=[C:16]([CH:23]2[CH2:24][CH2:25]2)[N:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 58497407(R)-3-(2-Cyclopropyl-5-nitro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497455(R)-3-(5-Amino-2-cyclopropyl-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(R)-3-(2-cyclopropyl-5-nitro-pyrimidine-4-ylamino)-3-phenyl-propionic acid ethyl ester (1.42 g, 4 mmol) was dissolved in ethyl acetate (30 ml). To the solution Pd/C (200 mg) was added and the mixture was stirred under hydrogen at 1 atm for 1 hour. The reaction mixture was filtered and evaporated to dryness to give oil. The residue was used as such for the next step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customto give oil

Sources & evidence

ORD record
ord-4b4cfa3349c94d508daab4d4e116568f
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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