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

HRID 1036168Notes

Reaction equation

HRID 1036168 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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2724541Prolinol, (R)-HCID 217666127-Chloro[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 58514386((R)-1-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylpyrrolidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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;

Workup

  1. customThe butanol is subsequently removed in vacuo
  2. additionmixed with water
  3. customare separated
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-783e26d661be47b1a284b824c43d8a5f
Source dataset
uspto-grants-2013_10
Patent number
US08546406B2

Reaction notes

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