Diisopropylethylamine → 7-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]-[1,2,4]-triazolo[1,5-a]pyrimidine

HRID 1036165Notes

Reaction equation

HRID 1036165 reaction equation
[C:1]1([O:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[N:24]2[N:25]=[CH:26][N:27]=[C:23]2[N:22]=[CH:21][CH:20]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[C:1]1([O:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:19]2[N:24]3[N:25]=[CH:26][N:27]=[C:23]3[N:22]=[CH:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 217666127-Chloro[1,2,4]triazolo[1,5-a]pyrimidineHCID 46845432(R)-2-(naphthalen-1-yloxymethyl)pyrrolidine

Product 1

HCID 468428387-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]-[1,2,4]-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

400 mg of (R)-2-(naphthalen-1-yloxymethyl)pyrrolidine, 500 mg of the 7-chloro-[1,2,4]triazolo[1,5-a]pyrimidine prepared above and 650 mg of N-ethyldiisopropylamine are heated at 130° C. in a microwave for 3 h in 40 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 640 mg of “A1”; m.p. 74-75°;

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-8a5b501d001b44a7a4ad7671b0cd41dd
Source dataset
uspto-grants-2013_10
Patent number
US08546406B2

Reaction notes

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