Bromobenzene → 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-1-phenyldihydropyrimidine-2,4(1H,3H)-dione

HRID 1245345Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH2:16][CH2:15][NH:14][C:13]1=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH2:16][CH2:15][N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]1=[O:19])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-dihydropyrimidine-2,4(1H,3H)-dione (100 mg, 0.35 mmol), from this Example step 1, bromobenzene (0.037 mL, 0.35 mmol), tris(dibenzylideneacetone)dipalladium (6.4 mg, 0.01 mmol), Xanthphos (0.0121 g, 0.021 mmol) and Cs2CO3 (0.171 g, 0.52 mmol) were combined in dry dioxane (1 mL) and stirred at 100° C. overnight in a sealed tube. The reaction mixture was partitioned between ethyl acetate and water. Combined organic extracts were washed with water and brine, dried over Na2SO4 and the solvent evaporated in vacuo. The product was purified by preparative TLC using ethyl acetate and hexane (30:70) to give the title compound.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washCombined organic extracts were washed with water and brine
dry with materialdried over Na2SO4
customthe solvent evaporated in vacuo
customThe product was purified by preparative TLC

Sources & evidence

ORD record: ord-0478d9619c3b4fb98c1a7376c1ed2c66
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125865B2

Reaction notes

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