Diisopropylethylamine → Ethyl (βR)-β-[(2-cyclopropyl-5-nitro-4-pyrimidinyl)amino]benzenepropanoate

HRID 2175201Notes

Reaction equation

HRID 2175201 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([CH:11]2[CH2:13][CH2:12]2)[N:3]=1.Cl.[CH2:15]([O:17][C:18](=[O:28])[CH2:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:16].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:17][C:18](=[O:28])[CH2:19][C@@H:20]([NH:27][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([CH:11]2[CH2:13][CH2:12]2)[N:3]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:16]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734508ethyl (3R)-3-amino-3-phenylpropanoate hydrochlorideHCID 56773419HCID 56773419, compound

Product 1

HCID 58497407Ethyl (βR)-β-[(2-cyclopropyl-5-nitro-4-pyrimidinyl)amino]benzenepropanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-Chloro-2-cyclopropyl-5-nitro-pyrimidine (597 mg, 3 mmol) in DMF (10 ml) was added (R)-3-Amino-3-phenyl-propionic acid ethyl ester hydro chloride (582 mg, 3 mmol). The mixture was stirred on ice for 5 minutes the DIPEA (580 mg, 4.5 mmol) was added. The solution was stirred at room temperature for one hour. TLC showed disappearance of the starting material. The reaction mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, evaporated to dryness to give oil, which was used as such for the next step.

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give oil, which

Sources & evidence

ORD record
ord-9c9de4620c994ebb884a5a6e39191328
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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