4-Pentyn-1-ol → HCID 58362540, compound

HRID 2361509Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=[C:4]2[N:3]=1.[CH2:15]([OH:20])[CH2:16][CH2:17][C:18]#[CH:19].CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.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>[N:3]1[C:4]2[N:5]([C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[C:19]#[C:18][CH2:17][CH2:16][CH2:15][OH:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine (40 mg, 0.2 mmol), pent-4-yn-1-ol (22 mg, 0.26 mmol), tetrakis(triphenylphosphine)palladium (23 mg, 0.02 mmol), DIPEA (50 mg, 0.4 mmol) in 2 mL dioxane was heated at 120° C. for 20 min in a microwave reactor and then cooled to rt. It was diluted with EtOAc (20 mL) and washed with brine (30 mL) and water (2×30 mL) and concentrated. The residue was purified by silica chromatography (EtOAc in DCM, 10% to 100%) to afford 5-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)pent-4-yn-1-ol as a yellow solid (28 mg, 56%). 1H NMR (400 MHz, CDCl3): δ 8.68 (d, J=6.8, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.57 (m, 1H), 7.42 (m, 1H), 6.95 (d, J=6.8 Hz, 1H), 3.85 (t, J=6 Hz, 2H), 2.82 (t, J=6.8 Hz, 2H), 1.93 (m, 2H); MS (ESI) m/z [M+H]+252.

Workup

temperaturecooled to rt
washwashed with brine (30 mL) and water (2×30 mL)
concentrationconcentrated
customThe residue was purified by silica chromatography (EtOAc in DCM, 10% to 100%)

Sources & evidence

ORD record: ord-5f44b41d251d401a91042ce3dfc1ac81
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691187B2

Reaction notes

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