2-Bromomesitylene → HCID 69433788, compound

HRID 598059Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[C:7]([CH3:10])[N:6]=[C:5]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[N:4]=1.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1Br.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:19]1([CH3:18])[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[NH:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[N:6][C:7]=1[CH3:10]

Participants

Conditions

Temperature: 115 °C

Procedure

4-Methoxy-6-methyl-N2,N2-dipropylpyrimidin-2,5-diamine (0.022 g, 0.092 mmol) was charged with 2,4,-6-trimethylbromobenzene (16.7 μL, 0.11 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (0.012 g, 0.018 mmol), sodium t-butoxide (0.012 g, 0.13 mmol) and tris(dibenzylideneacetone) dipalladium (0) (Pd2(dba)3) (0.017 g, 0.018 mmol). The reagents were diluted in 1 mL of toluene and heated at 115° C. for 1.5 h. The solution was cooled and flash chromatographed (5% ethyl acetate/hexanes) to give 0.019 g (58%) of the title compound as an oil.

Workup

temperatureThe solution was cooled
customflash chromatographed (5% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-1b27ca9ddf2d4723b29afbe8b8641f7a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

Loading…