Dimethylcarbamoyl Chloride → HCID 67527687, compound

HRID 2388640Notes

Reaction equation

HRID 2388640 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH:7]([NH:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[N:18]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:31])[CH:7]([NH:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[N:18]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:41](=[O:42])[N:40]([CH3:44])[CH3:39])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 21023684HCID 21023684, compound

Product 1

HCID 67527687HCID 67527687, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-diethylamino-5-nitropyrimidin-4-ylamino)-3-(4-hydroxy-phenyl)propionic acid t-butyl ester (31.80 g, 0.074 mol) in CH2Cl2 (600 mL) was added DMAP (9.00 g, 0.074 mol). After 5 minutes triethylamine (10.23 mL, 0.074 mol) was added dropwise. N,N-dimethylcarbamyl chloride (13.83 mL, 0.110 mol) was added dropwise, and the reaction was heated to reflux overnight. The reaction mixture was concentrated in vacuo and taken up in EtOAc (1 L). The organic phase was washed with 0.5 M citric acid (3×250 mL), sat. NaHCO3 (3×250 mL), brine (1×250 mL), dried (MgSO4), filtered, and concentrated in vacuo to yield 37.0 g (99%) the title compound as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washThe organic phase was washed with 0.5 M citric acid (3×250 mL), sat. NaHCO3 (3×250 mL), brine (1×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a463d67b1b749dfbcf580d410f94d9a
Source dataset
uspto-grants-2012_09
Patent number
US08269009B2

Reaction notes

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