Sodium Bicarbonate → HCID 86637511, compound

HRID 1676803Notes

Reaction equation

HRID 1676803 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]([F:17])([F:16])[CH2:6][NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]([F:17])([F:16])[CH2:6][N:7]([C:22]1[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 58015072HCID 58015072, compound

Product 1

HCID 86637511HCID 86637511, compoundYield 135.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 0.57 g (0.0022 mole) of 2,2-difluoro-3-phenethylamino-propionic acid ethyl ester in 1 mL of ethyl acetate was added over 5 minutes to a cooled (0 degrees) mixture of 0.43 g (0.0022 mole) of 2,4-dichloro-5-nitro-pyrimidine, 0.75 g (0.0088 mole) of sodium bicarbonate and 6 mL of ethyl acetate. The cooling bath was removed and the mixture stirred for 17 hours at room temperature. Activated charcoal was added and after stirring briefly, the mixture was filtered through a pad of Celite, washing the filter pad with ethyl acetate. The filtrate was concentrated under reduced pressure to give 1.24 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-phenethyl-amino]-2,2-difluoro-propionic acid ethyl ester (IV-275) as a yellow thick oil. This material was used directly in the next step without further purification.

Workup

  1. temperaturea cooled
  2. customThe cooling bath was removed
  3. additionActivated charcoal was added
  4. stirringafter stirring briefly
  5. filtrationthe mixture was filtered through a pad of Celite
  6. washwashing the filter pad with ethyl acetate
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-01fa59a6e2734e81bbd995d2d995cafb
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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