Sodium Bicarbonate → HCID 86637525, compound

HRID 1676836Notes

Reaction equation

HRID 1676836 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([Cl:13])([Cl:12])[CH2:5][NH:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]([Cl:12])([Cl:13])[CH2:5][N:6]([C:18]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 58015015HCID 58015015, compound

Product 1

HCID 86637525HCID 86637525, compoundYield 143.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1.5 g (0.0063 mole) of 2,2-dichloro-3-cyclopentylamino-propionic acid methyl ester in 3 mL of ethyl acetate was added over 5 minutes to a cooled (0 degrees) mixture of 0.81 g (0.0042 mole) of 2,4-dichloro-5-nitro-pyrimidine, 1.76 g (0.02 mole) of sodium bicarbonate and 15 mL of ethyl acetate. The cooling bath was removed and the mixture stirred for 24 hours at room temperature and then 24 hours at 75 degrees. 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 2.4 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dichloro-propanoic acid methyl ester (IV-298) 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. custom24 hours
  4. customat 75 degrees
  5. additionActivated charcoal was added
  6. stirringafter stirring briefly
  7. filtrationthe mixture was filtered through a pad of Celite
  8. washwashing the filter pad with ethyl acetate
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70a8da497bbc4cd4bcb6a4382ea4174d
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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