Potassium Carbonate → HCID 89561488, compound

HRID 530103Notes

Reaction equation

HRID 530103 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.Cl.[CH3:13][O:14][C:15](=[O:19])[C@@H:16]([CH3:18])[NH2:17].C(=O)([O-])[O-].[K+].[K+]>CCOCC.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C@@H:16]([C:15]([O:14][CH3:13])=[O:19])[CH3:18])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 11182647Methyl D-alaninate hydrochloride

Product 1

HCID 89561488HCID 89561488, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,4-dichloro-5-nitropyrimidine (17.5 g, 90 mmol) in ether (100 mL) at —OC was added a solution of D-alanine methyl ester hydrochloride (12 g, 85.96 mmol) in water (50 mL). To the resulting mixture was added potassium carbonate (71.2 g, 515.5 mmol) in portions with vigorous stirring. Then the reaction was allowed to warm up to rt and stirred for 16 h. The precipitated solid was filtered to afford desired product as yellow solid (4 g). Ether layer was separated from filtrate, the aqueous layer was extracted with ether (50 mL×3). Combined ether layers were dried (Na2SO4), evaporated to give a crude residue, which was then purified by silica gel flash chromatography to give another 2.7 g of desired product. 1HNMR (300 MHz, CDCl3): δ 1.61 (d, J=7.2 Hz, 3H), 3.82 (s, 3H), 4.90-5.0 (m, 1H), 8.75 (br s 1H) and 9.07 (s, 1H).

Workup

  1. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-d22e8f8702264867bc2f59029fff681d
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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