Water → 2-chloro-4-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]pyrimidine

HRID 1036166Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.[C:18]1([O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][NH:31]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.O>C(O)(C)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:31]2[CH2:32][CH2:33][CH2:34][C@@H:30]2[CH2:29][O:28][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

327 mg of 2,4-dichloropyrimidine are dissolved in 20 ml of isopropanol, and 0.8 ml of N-ethyldiisopropylamine and 500 mg of (R)-2-(naphthalen-1-yloxymethyl)pyrrolidine are added. This mixture is warmed at 80° C. for 6 h. After cooling, the batch is poured into 40 ml of water and 40 ml of ethyl acetate. After phase separation, the organic phase is dried, evaporated and chromatographed on silica gel, giving 480 mg of 2-chloro-4-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]pyrimidine as colourless oil;

Workup

temperatureAfter cooling
customAfter phase separation
customthe organic phase is dried
customevaporated
customchromatographed on silica gel

Sources & evidence

ORD record: ord-9e861771b4794dd2a7630687df19aba4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546406B2

Reaction notes

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