1,4-Dioxane → 4-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde

HRID 2067868Notes

Reaction equation

HRID 2067868 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.O1[CH2:22][CH2:21][O:20][CH2:19]C1>CCCC[N+](CCCC)(CCCC)CCCC.[I-].[O-2].[Mn+4].[O-2]>[CH3:19][O:20][C:21]1[CH:22]=[CH:11][C:10]([C:2]2[CH:3]=[N:4][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=3)=[N:6][CH:7]=2)=[CH:9][CH:14]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 57632949[4-(5-Bromo-pyrimidin-2-ylamino)-phenyl]-methanol

Product 1

HCID 576326954-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 178418406HCID 178418406, compoundCatalyst

Conditions

Temperature
130 °C

Procedure

To a solution of [4-(5-bromo-pyrimidin-2-ylamino)-phenyl]-methanol 15 (0.94 mmol) in dioxane (2 mL) is added manganese (IV) oxide (4.7 mmol) and TBAI (0.06 mmol). The reaction mixture is heated in a microwave oven at 130° C. for 30 min. Purification by silica gel chromatography using hexane:EtOAc=1:1 affords 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-benzaldehyde 16. 1H NMR (400 MHz, d6-DMSO) δ 10.45 (s, 1H), 9.85 (s, 1H), 8.72 (s, 2H), 7.96 (d, J=8.4 Hz, 2H), 7.85 (d, J=8.4 Hz, 2H). MS (m/z) (M+1)+: 278.0, 280.0.

Workup

  1. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-5a85d17efe1b4383960d9750713ce464
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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