Toluene → HCID 59507837, compound

HRID 1512148Notes

Reaction equation

HRID 1512148 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1.[C:24](Cl)(Cl)=[O:25].C1(C)C=CC=CC=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[CH2:15][CH2:16][N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 59507594HCID 59507594, compound

Product 1

HCID 59507837HCID 59507837, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-(6-chloro-2-morpholinopyrimidin-4-yl)-N2-phenylethane-1,2-diamine (100 mg, 0.3 mmol) in DCM (15 mL) at 0° C. under nitrogen, a solution of phosgene in toluene (1.89 M, 0.32 mL, 0.6 mmol) was slowly added. After 20 minutes, the reaction was allowed to warm to RT. After 18 hours, DIEA (0.42 mL, 2.4 mmol) was added and the reaction solution was heated to 40-50° C. for 40 hours. The reaction mixture was evaporated under reduced pressure and the crude product was purified by silica gel chromatography eluting with 70% EtOAc/hexane to give 1-(6-chloro-2-morpholinopyrimidin-4-yl)-3-phenylimidazolidin-2-one as a white solid (94 mg, 87%). LC/MS (m/z): 360.1 (MH+), Rt 3.41 minutes.

Workup

  1. waitAfter 18 hours
  2. temperaturethe reaction solution was heated to 40-50° C. for 40 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe crude product was purified by silica gel chromatography
  5. washeluting with 70% EtOAc/hexane

Sources & evidence

ORD record
ord-c14dcf98623340ef9d1e6aeb260fe2cf
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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