Triethylamine → 4-Phenyl-6-phenylethynylpyrimidin-2-ylamine

HRID 1161677Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH2:14])[N:3]=1.C(N(CC)CC)C.[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)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>[C:8]1([C:6]2[CH:7]=[C:2]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:3]=[C:4]([NH2:14])[N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-chloro-6-phenylpyrimidin-2-ylamine (2.0 g, 9.7 mmol), (PPh3)2PdCl2 (204 mg, 0.29 mmol), triethylamine (4.9 g, 48.5 mmol) in DMF (10 mL) was stirred at 25° C. for 0.5 hour under a nitrogen atmosphere. Then phenylacetylene (1.29 g, 12.70 mmol) was added to it and the mixture was stirred at 100° C. for 4 hours under a nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C., diluted with water (20 mL) and extracted with EtOAc (3×25 mL). The organic layers were collected, combined, washed with water (30 mL), dried over anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography using EtOAc-petroleum ether to give the desired product.

Workup

stirringthe mixture was stirred at 100° C. for 4 hours under a nitrogen atmosphere
temperatureThe mixture was cooled to temperature in the range of 20-40° C.
extractionextracted with EtOAc (3×25 mL)
customThe organic layers were collected
washwashed with water (30 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-c50ed9192eb9480a95a66f39c2446539
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820654B2

Reaction notes

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