Cesium carbonate → HCID 86686749, compound

HRID 1403117Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:4]=1.Br[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:26].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:26][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:17]=1[NH:9][C:7]1[CH:6]=[C:5]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-(methylsulfanyl)-6-(morpholin-4-yl)pyrimidin-4-amine (500 mg), 2-bromo-1-methyl-3-nitrobenzene (1 g), tris(dibenzylideneacetone)dipalladium (0) (202 mg), (9,9-dimethyl-9H-xanthen-4,5-diyl)bis(diphenylphosphine) (192 mg), and cesium carbonate (1.0 g) in toluene was stirred in a microwave reactor at 140° C. for 1 hour. The reaction mixture was filtered through celite and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain N-(2-methyl-6-nitrophenyl)-2-(methylsulfanyl)-6-(morpholin-4-yl)pyrimidin-4-amine (756 mg) as a yellow powder.

Workup

filtrationThe reaction mixture was filtered through celite and
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-6b17091ce5804bcc8523b25ec123bc51
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912180B2

Reaction notes

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