2-[(Hept-6-yn-2-yl)oxy]oxane → 5-Benzyloxy-2-[4-(6-tetrahydropyranyloxy-1-heptynyl)phenyl]pyrimidine

HRID 1956086Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH:29]([CH3:35])[CH2:30][CH2:31][CH2:32][C:33]#[CH:34]>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)I.C(N(CC)CC)C>[CH2:15]([O:14][C:11]1[CH:10]=[N:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]#[C:33][CH2:32][CH2:31][CH2:30][CH:29]([O:28][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][O:22]3)[CH3:35])=[CH:3][CH:4]=2)=[N:13][CH:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In a reactor equipped with a stirrer and a thermometer, 2-(4-bromophenyl)-5-benzyloxypyrimidine, 6-tetrahydropyranyloxy-1-heptyne, dichlorobis(triphenylphosphine)palladium, copper iodide, triphenylphosophine and triethylamine are charged and heated up to 90° C. to carry out a reaction for 8 hours. After extraction with toluene and washing with water, the mixture is evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography to obtain 5-benzyloxy-2-[4-(6-tetrahydropyranyloxy-1-heptynyl)phenyl]pyrimidine.

Workup

customIn a reactor equipped with a stirrer
customa reaction for 8 hours
extractionAfter extraction with toluene
washwashing with water
customthe mixture is evaporated under reduced pressure
customA resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-044561e80c014bfbb56490ce05acc607
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05779934

Reaction notes

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