Trimethylsilylacetylene → 4-{2-Methyl-6-[2-(trimethylsilyl)ethynyl]-1,3-benzodiazol-1-yl}-1,3,5-triazin-2-amine

HRID 1398699Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C(N(CC)CC)C>[CH3:10][C:8]1[N:7]([C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[C:6]2[CH:18]=[C:2]([C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4-(6-bromo-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine (250 mg, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol), copper(I) iodide (11 mg, 0.06 mmol) and ethynyl(trimethyl)silane 0.230 ml, 1.51 mmol) was added triethylamine (2.6 mL). The mixture was purged with nitrogen for 2 minutes and was stirred at 80° C. for 15 min in the microwave. LC-MS shows 50% conversion. The mixture was retreated with another equivalent of tetrakis(triphenylphosphine)palladium (70 mg) copper(I) iodide (11 mg) and ethynyl(trimethyl)silane (0.230 ml). Heating in the microwave at 90° C. was continued for another

Workup

customThe mixture was purged with nitrogen for 2 minutes
temperatureHeating in the microwave at 90° C.

Sources & evidence

ORD record: ord-36a62ea70dac43158d5e362abc007cd7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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