Dichloromethane → HCID 58784302, compound

HRID 1374687Notes

Reaction equation

HRID 1374687 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:25]2C=[CH:29][CH:28]=[CH:27][C:26]=2Cl)[N:8]([CH2:20][CH2:21][CH2:22][NH:23][CH3:24])[C:9](=[O:19])[NH:10][C:11]=1[CH2:12][O:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])=[O:5])[CH3:2].C(N(CC)CC)C.[C:39](Cl)(=[O:48])[CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[CH2:50]([Cl:52])Cl>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:50]=2[Cl:52])[N:8]([CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[C:39](=[O:48])[CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:9](=[O:19])[NH:10][C:11]=1[CH2:12][O:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 58784309HCID 58784309, compound

Product 1

HCID 58784302HCID 58784302, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude 6-(2-azido-ethoxymethyl)-4-(2-chloro-phenyl)-3-(3-methylamino-propyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (40 mg, 0.89 mmol) in CH2Cl2 (2 mL) was added triethylamine (25 μl, 18 mg, 0.179 mmol) followed by a solution of hydrocinnamoyl chloride (25 mg, 0.148 mmol) in CH2Cl2 (0.5 ml). After 3 h, the mixture was taken up in EtOAc (50 mL) and then washed with H2O (25 mL) and brine (25 mL). The organic extract was dried (Na2SO4), filtered, concentrated in vacuo. The crude product was purified by chromatography using the ISCO Combiflash SQ16× (35 g Redisep silica gel, 20 to 100% EtOAC in hexanes for 20 min, hold at 100% EtOAc for 15 min at 30 mL/min) to afford 27.6 mg (53%) of the purified material as a thick oil.

Workup

  1. washwashed with H2O (25 mL) and brine (25 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-08aea185a4724ae2a709ccf891a440d3
Source dataset
uspto-grants-2007_01
Patent number
US07166603B2

Reaction notes

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