Piperazine → 6-Chloro-7-(4-hydroxypiperidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

HRID 2242802Notes

Reaction equation

[N:1]1([C:6]2[C:15]3[C:10](=[N:11][C:12](Cl)=[C:13]([Cl:16])[N:14]=3)[N:9]=[C:8](Cl)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C.[NH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>O1CCOCC1>[Cl:16][C:13]1[N:14]=[C:15]2[C:10](=[N:11][C:12]=1[N:23]1[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]1)[N:9]=[C:8]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[N:7]=[C:6]2[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

a)+b) 80 mg (0.26 mmol) 4-pyrrolidin-1-yl-2,6,7-trichloro-pteridine are dissolved in 5 ml dioxane and combined with 29 mg (0.29 mmol) 4-hydroxypiperidin and 49 μl (0.37 mmol) diisopropylethylamine. The mixture is stirred for approx. 16 h at 40° C. The reaction mixture is then slowly added dropwise to a solution of 113 mg (1 mmol) piperazine in 15 ml dioxane at a temperature of 80° C. The mixture is stirred for approx. 16 h at 80° C., cooled to ambient temperature and then poured onto ice water. It is extracted with dichloromethane, the organic phase is dried on sodium sulphate and the solvent is eliminated in vacuo. The residue is taken up in some dichloromethane and combined with petroleum ether, the precipitate formed is suction filtered. Yield 58 mg (53% of theoretical).

Workup

stirringThe mixture is stirred for approx. 16 h at 80° C.
temperaturecooled to ambient temperature
additionpoured onto ice water
extractionIt is extracted with dichloromethane
customthe organic phase is dried on sodium sulphate
customthe precipitate formed
filtrationfiltered

Sources & evidence

ORD record: ord-22a8f81636a94bd8bd84686d8d54125e
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674788B2

Reaction notes

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