Diisopropylamine → HCID 67247364, compound

HRID 1970395Notes

Reaction equation

Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:16]4[CH:17]=[N:18][CH:19]=[N:20][CH:21]=4)=[CH:9][CH:10]=3)[C:5]3([CH2:25][S:24][C:23]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:22]3)[C:4]=2[CH:3]=1.[CH3:31][C:32]([CH3:36])([CH3:35])[C:33]#[CH:34].C(NC(C)C)(C)C>[Cu]I.CN(C=O)C>[C:27]([NH:26][C:23]1[S:24][CH2:25][C:5]2([N:22]=1)[C:4]1[CH:3]=[C:2]([C:34]#[C:33][C:32]([CH3:36])([CH3:35])[CH3:31])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:16]2[CH:21]=[N:20][CH:19]=[N:18][CH:17]=2)=[CH:9][CH:10]=1)([CH3:29])([CH3:28])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

A resealable tube was charged with (t-4)-tetrakis(triphenylphosphine)palladium (27.1 mg, 0.023 mmol), copper(i) iodide (8.94 mg, 0.047 mmol),2′-bromo-N-tert-butyl-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine (113 mg, 0.235 mmol), 3,3-dimethylbut-1-yne (144 μL, 1.174 mmol), diisopropylamine (669 μL, 4.69 mmol) and DMF (1.9 mL). The mixture was heated at 80° C. After 18 hrs, the mixture was cooled to RT, filtered through celite with EtOAc, and concentrated in vacuo. The residue was adsorbed onto silica gel and purified by silica gel chromatography using 30-75% Hexanes:EtOAc to afford N-tert-butyl-2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine as an off-white foam. MH+=483.2.

Workup

temperaturethe mixture was cooled to RT
filtrationfiltered through celite with EtOAc
concentrationconcentrated in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-44a953ddd59741d587b22ed195229153
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426447B2

Reaction notes

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