Phenyl chloroformate → HCID 59379902, compound

HRID 2353687Notes

Reaction equation

HRID 2353687 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]3[CH3:24])[N:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:30]1([O:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1>[CH3:24][C@H:19]1[CH2:20][O:21][CH2:22][CH2:23][N:18]1[C:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:37]([O:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:38])=[CH:7][CH:6]=2)[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380147HCID 59380147, compound

Product 1

HCID 59379902HCID 59379902, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(4-aminophenyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate (400 mg) was dissolved in dioxane (10 mL) and sodium bicarbonate (154 mg) and phenylchloroformate (0.154 mL) added dropwise. The mixture was stirred at RT for 16 hours then the dioxane removed under reduced pressure and the residue partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was dried over magnesium sulphate, filtered and evaporated to give the desired material as a brown foam (624 mg).

Workup

  1. customthe dioxane removed under reduced pressure
  2. customthe residue partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8a6b635da1d64050964acf1250296393
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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