Piperazine → 6-chloro-7-((R)-3-hydroxypyrrolidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

HRID 2242803Notes

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][C@@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.C(N(C(C)C)CC)(C)C.[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>O1CCOCC1>[Cl:16][C:13]1[N:14]=[C:15]2[C:10](=[N:11][C:12]=1[N:22]1[CH2:23][CH2:24][C@@H:20]([OH:19])[CH2:21]1)[N:9]=[C:8]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]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 72 mg (0.58 mmol) (R)-3-hydroxypyrrolidin and 100 μl (0.75 mmol) diisopropylethylamine. The mixture is stirred for approx. 30 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 purified by chromatography. Yield 68.8 mg (65% 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 residue is purified by chromatography

Sources & evidence

ORD record: ord-d011efb0e73d4f40bb6c6989c6fec150
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674788B2

Reaction notes

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