Potassium Carbonate → HCID 89561346, compound

HRID 530097Notes

Reaction equation

HRID 530097 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.[CH:12]1([NH:18][C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CCOCC>[Cl:1][C:2]1[N:7]=[C:6]([N:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])[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 66661039N-Cyclohexyl-D-alanine methyl ester

Product 1

HCID 89561346HCID 89561346, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (28.5 g, 146.9 mmol) in ether (200 mL) was added methyl N-cyclohexyl-D-alaninate (17.0 g, 91.8 mmol) at −10° C. To the resulting solution was then added aqueous potassium carbonate (19.0 g in 100 mL water) drop wise while maintaining the temperature below 0° C. Reaction mixture was then warmed to rt and stirred at rt for 16 h. The organic layer was separated and the aqueous layer was extracted with ether (3×75 mL). Combined ether solution was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel flash chromatography using ethyl acetate-hexane mixture (v:v=5:95) as eluent to give titled compound (yield, 41%). 1HNMR (300 MHz, CDCl3): δ 1.06-1.29 (m, 3H), 1.43-1.53 (m, 2H), 1.58 (s, 1H), 1.64 (d, J=6.9 Hz, 3H), 1.90-1.82 (m, 2H), 2.02-1.98 (m, 1H), 2.17-2.14 (m, 1H), 3.09-3.01 (m, 1H), 3.73 (s, 3H), 4.13 (q, J=6.9 Hz, 1H), 8.59 (s, 1H).

Workup

  1. customReaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ether (3×75 mL)
  4. washCombined ether solution was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-7e9e6da4ee614519a5d674b20ac7599f
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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