Carbon Dioxide → HCID 10955701, compound

HRID 379538Notes

Reaction equation

HRID 379538 reaction equation
C(OC([N:8]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:9]1[C:14]([Cl:15])=[C:13]([CH2:16][CH3:17])[N:12]=[CH:11][N:10]=1)=O)(C)(C)C.C(=O)=O.FC(F)(F)C(O)=O>ClC(Cl)C>[Cl:15][C:14]1[C:9]([NH:8][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:10][CH:11]=[N:12][C:13]=1[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 6422Trifluoroacetic acidHCID 57140763HCID 57140763, compound

Product 1

HCID 10955701HCID 10955701, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

20.7 g (0.61 mmol) of 4-(tert-butoxycarbonylpiperidin-4-ylamino)-5-chloro-6-ethylpyrimidine (Example A) were dissolved in 100 ml of dichloroethane and 148.0 g of trifluorocetic acid were added slowly. After the evolution of CO2 had ceased, stirring was continued for 2 more hours. After the solvent and the trifluoroacetic acid had been stripped off, the mixture was concentrated and the residue was taken up in dichloromethane/water. After the mixture had been rendered weakly alkaline by addition of dilute sodium hydroxide solution, the organic phase was separated off, dried and concentrated. This gave 12.3 g (83.9% of theory) of a yellow solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additionby addition of dilute sodium hydroxide solution
  3. customthe organic phase was separated off
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-978f022d57634d4099667714e1b0a7b4
Source dataset
uspto-grants-2001_10
Patent number
US06300333B1

Reaction notes

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