Diisopropylethylamine → ((R)-1-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methanol

Reaction equation

[NH:1]1[CH2:7][CH2:6][CH2:5][C@@H:2]1[CH2:3][OH:4].Cl[C:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[N:12]=[CH:11][CH:10]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[N:15]1[N:14]2[C:9]([N:1]3[CH2:7][CH2:6][CH2:5][C@@H:2]3[CH2:3][OH:4])=[CH:10][CH:11]=[N:12][C:13]2=[N:17][CH:16]=1

Participants

Procedure

1 g of commercially available (D)-prolinol, 1.5 g of 7-chloro-[1,2,4]triazolo-[1,5-a]pyrimidine and 2.6 g of N-ethyldiisopropylamine are heated at 130° C. in a microwave for 3 h in 60 ml of 1-butanol. The butanol is subsequently removed in vacuo, the residue is taken up in ethyl acetate, mixed with water, adjusted to pH 12 using 1 N NaOH solution, phases are separated, the organic phase is dried over sodium sulfate, evaporated and chromatographed on silica gel, giving 1.7 g of ((R)-1-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methanol as beige crystals;