2,4-Hexadienal → 4-ethoxy-7-(4-[{2E,4E}-1-hydroxyhexa-2,4-dienyl]phenyl)-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

HRID 556402Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:30])[C:11]3[C:16]4[N:17]=[C:18]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[N:19]=[C:20]([O:21][CH2:22][CH3:23])[C:15]=4[S:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[Li]CCCC.[CH:36](=[O:42])/[CH:37]=[CH:38]/[CH:39]=[CH:40]/[CH3:41]>C1COCC1>[CH2:22]([O:21][C:20]1[C:15]2[S:14][C:12]3[N:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH:36]([OH:42])/[CH:37]=[CH:38]/[CH:39]=[CH:40]/[CH3:41])=[CH:3][CH:4]=4)[N:9]=[C:10]([CH3:30])[C:11]=3[C:16]=2[N:17]=[C:18]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:19]=1)[CH3:23]

Participants

Conditions

Temperature: -10 °C

Procedure

200 mg (0.4 mmol) 7-(4-bromophenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d′]dipyrimidine was mixed at −80° C. in 50 ml THF with 0.48 ml (1.2 mmol) 2.5 M BuLi solution. After 15 min at this temperature, 112 mg (1.2 mmol) (2E,4E) hexadienal was added. Subsequently, the reaction mixture was heated to −10° C. and the reaction was terminated by addition of 10 ml saturated NaHCO3. The organic solvent was removed and the aqueous phase was extracted with CH2Cl2. Following flash chromatographic purification (CH2Cl2/methanol, 8:2) 130 mg (63%) of the title compound was obtained. ESI-MS [m/z]: 503, melting point: 149-150° C.

Workup

customthe reaction was terminated by addition of 10 ml saturated NaHCO3
customThe organic solvent was removed
extractionthe aqueous phase was extracted with CH2Cl2
customchromatographic purification (CH2Cl2/methanol, 8:2) 130 mg (63%) of the title compound
customwas obtained

Sources & evidence

ORD record: ord-77ed455c0b5948c18958643106953be5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058285B2

Reaction notes

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