Methane, dichloromethoxy- → HCID 10178654, compound

HRID 2250996Notes

Reaction equation

[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[N:11]([C:16]1[CH:21]=[C:20]([NH:22][CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[N:19]=[C:18]([CH3:28])[N:17]=1)[CH2:10][CH2:9]2.[CH:29]([O:32]C)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[N:11]([C:16]1[C:21]([CH:29]=[O:32])=[C:20]([NH:22][CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[N:19]=[C:18]([CH3:28])[N:17]=1)[CH2:10][CH2:9]2

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of AlCl3 (736 mg, 5.44 mmol) in CHCl3 (5 mL) a solution of 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.46 g, 4 mmol) in CHCl3 was added at 0° C., followed by Cl2CHOMe (0.4 mL, 4.4 mmol). The reaction was stirred at 0° C. for 2 h and at 20° C. for 16 h. Then an additional amount of Cl2CHOMe was added (0.2 mL, 2.2 mmol) and the reaction was continued for 26 h. The mixture was poured into ice/water (50 mL) and after quenching it was basified with 1 N NaOH, extracted with EtOAc (2×100 mL each) and the combined organic extracts were washed with water, brine, dried over (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent to give the product 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-formyl-2-methylpyrimidine (470 mg, 30% yield).

Workup

additionwas added at 0° C.
waitthe reaction was continued for 26 h
customafter quenching it
extractionextracted with EtOAc (2×100 mL each)
washthe combined organic extracts were washed with water, brine
dry with materialdried over (MgSO4)
customThe residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent

Sources & evidence

ORD record: ord-bec63cb3b8484250accd055ec51bca10
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319100B2

Reaction notes

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