Potassium Carbonate → HCID 89560709, compound

HRID 530100Notes

Reaction equation

HRID 530100 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]([C:27]([O:29][CH3:30])=[O:28])([CH3:26])[NH:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:20]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([CH3:18])([C:27]([O:29][CH3:30])=[O:28])[CH3:26])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 43725945HCID 43725945, compound

Product 1

HCID 89560709HCID 89560709, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred suspension of 2,4-dichloro-5-nitropyrimidine (7.5 g, 38.5 mmol), anhydrous potassium carbonate (10.0 g) in dry acetone (150 mL) was added a solution of methyl 2-methyl-N-(3-methylbutyl)alaninate (5.6 g, 30.0 mmol) in dry acetone (9 mL) at 0° C. The reaction was then allowed to warm up to room temperature and stirred at rt for 16 h. The reaction mixture was filtered and evaporated. The residue was purified by flash chromatography on silica gel (eluent: ethyl acetate-hexane mixture (v:v=5:95)) to give titled product (yield: 15%). 1HNMR (300 MHz, CDCl3): δ 0.85 (s, 3H), 0.88 (s, 3H), 1.30-1.36 (m, 2H), 1.60-1.65 (m, 7H), 3.37-3.42 (m, 2H), 3.72 (s, 3H) and 8.56 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customThe residue was purified by flash chromatography on silica gel (eluent: ethyl acetate-hexane mixture (v:v=5:95))

Sources & evidence

ORD record
ord-e27f0094667146fa91c9129b2e87c85b
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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