Ammonia → HCID 59465198, compound

HRID 1714838Notes

Reaction equation

HRID 1714838 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:15][C:16]2[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=2)[C@@H:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:26]([O-:28])=[O:27])=[CH:4][N:3]=1.[NH3:29]>C1COCC1>[NH2:29][C:2]1[N:7]=[C:6]([N:8]([CH2:15][C:16]2[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=2)[C@@H:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:26]([O-:28])=[O:27])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59465211HCID 59465211, compound2×

Product 1

HCID 59465198HCID 59465198, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl]amino]propanoate (Intermediate 3)(1.0 g, 2.44 mmol) in THF (30 mL) was treated with ammonia (28% in water, 3 mL). The reaction mixture was stirred at room temperature for 2.5 hours, then partitioned between DCM and water. The organic solution was dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified by MPLC on silica using gradient elution (30% ethyl acetate/isohexane to 100% ethyl acetate). Intermediate 1 was obtained as a yellow foam (770 mg, 81%); 1H NMR spectrum: (400 MHz CDCl3) δ1.63 (3H, d), 2.10 (3H, s), 2.22 (3H, s), 3.65 (3H, s), 3.74 (3H, s), 4.44 (1H, d), 4.64-4.72 (2H, m), 5.24 (2H, s), 8.14 (1H, s), 8.66 (1H, s); Mass spectrum: (M+H)+ 391.

Workup

  1. custompartitioned between DCM and water
  2. dry with materialThe organic solution was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by MPLC on silica using gradient elution (30% ethyl acetate/isohexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-fb2c99f1de834b00898bdaafda5801f0
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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