Triethylamine → N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine

HRID 1042742Notes

Reaction equation

Br[C:2]1[C:3]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:4][C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23]>[Cu]I.C(#N)C>[CH3:9][NH:8][C:5]1[N:4]=[C:3]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[C:2]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A 75 mL thick wall glass tube with a teflon screw cap was charged with 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine (0.995 g, 3.68 mmol), acetonitrile (9 mL), triethylamine (3.00 ml, 3.68 mmol), dichlorobistriphenylphosphine palladium(II) (0.259 g, 0.368 mmol), copper(I) iodide (0.0351 g, 0.184 mmol), and ethynyltrimethylsilane (0.362 g, 3.68 mmol). The tube was capped and heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine. MS m/z=288 [M+H]+. Calc'd for C14H17N3SSi: 287.

Workup

customThe tube was capped
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-99db30a14cf4408e9b3dbda460d31521
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Reaction notes

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