Triethylamine → HCID 86712705, compound

HRID 1779062Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11])#[CH:2].CCN(CC)CC.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([O:29][CH3:30])=[CH:24][N:23]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CCOC(C)=O.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>[Cl:21][C:22]1[N:27]=[C:26]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:25]([O:29][CH3:30])=[CH:24][N:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of methyl 2-(2-ethynylphenyl)acetate (K1) (0.35 g, 2.0 mmol) in DMF (3 mL) and Et3N (0.70 mL, 5.0 mmol) was added to a mixture of 2,4-dichloro-5-methoxypyrimidine (0.30 g, 1.7 mmol), PdCl2(PPh3)2 (0.12 g, 0.17 mmol), CuI (0.032 g, 0.17 mmol) and PPh3 (0.044 g, 0.17 mmol) in DMF (3 mL). The resulting mixture was heated under microwave irradiation at 120° C. for 15 minutes, then diluted with EtOAc and passed through a plug of Celite, washing with EtOAc (50 mL). The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-25% EtOAc in hexanes) to give the title compound A98 as a pale yellow solid (0.38 g, 72%); 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.65 (dd, J=7.6, 1.0 Hz, 1H), 7.46-7.29 (m, 3H), 4.03 (s, 3H), 3.99 (s, 2H), 3.71 (s, 3H). LCMS-A: rt 5.92 min; m/z 317.1 [M+H]+.

Workup

washwashing with EtOAc (50 mL)
customThe volatiles were removed in vacuo
customthe residue was purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0c46a484c76642ee89744c9edd25e366
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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