Triethylamine → HCID 86712626, compound

HRID 1778957Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][C:38]([O:40][CH3:41])=[O:39])#[CH:30].CCN(CC)CC>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:30]#[C:29][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 4-chloro-2-methylthiopyrimidine (200 μL, 1.72 mmol), PdCl2(PPh3)2 (121 mg, 0.172 mmol), CuI (33.0 mg, 0.172 mmol), PPh3 (45.0 mg, 0.172 mmol), methyl 2-(2-ethynyl phenyl)acetate (K1) (359 mg, 1.08 mmol) and Et3N (0.938 mL) in THF (6 mL) was heated at 100° C. under microwave irradiation for 10 minutes. The volatiles were removed in vacuo and the resultant residue adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-40% EtOAc in petroleum benzine 40-60° C., then Biotage Isolera, SiO2 cartridge, 0-40% EtOAc in DCM) to give the title compound A1 as a yellow oil (323 mg, 63%); 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=5.0 Hz, 1H), 7.63 (dd, J=7.6, 1.1 Hz, 1H), 7.44-7.29 (m, 3H), 7.12 (d, J=5.0 Hz, 1H), 3.92 (s, 2H), 3.71 (s, 3H), 2.59 (s, 3H).

Workup

customThe volatiles were removed in vacuo
custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-40% EtOAc in petroleum benzine 40-60° C.

Sources & evidence

ORD record: ord-8e3f27ce8aa041afaab350884f65ba8d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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