2-Hydrazino-1,4,5,6-tetrahydropyrimidine hydroiodide → 3-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

HRID 273124Notes

Reaction equation

HRID 273124 reaction equation
I.[NH:2]1[CH2:7][CH2:6][CH2:5][N:4]=[C:3]1[NH:8][NH2:9].Cl.[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[N:15]1[CH:16]=[CH:17][C:12]([C:11]2[N:4]3[CH2:5][CH2:6][CH2:7][NH:2][C:3]3=[N:8][N:9]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 122615182-Hydrazino-1,4,5,6-tetrahydropyrimidine hydroiodideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidineYield 18%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 750 mg (3.1 mmol) (1,4,5,6-tetrahydro-pyrimidin-2-yl)-hydrazine hydroiodide (ref. Krezel, Izabella; Pharmazie; EN; 49; 1; 1994; 27-31) and 552 mg (3.1 mmol) isonicotinoyl chloride hydrochloride in 3 ml pyridine was heated at 120° C. over night. The reaction mixture was cooled and diluted with K2CO3(sat) and extracted with 3×10 ml chloroform. The combined organic extracts were dried and concentrated. Flashchromatography (CH2Cl2/MeOH 10:1) afforded 83 mg (18%) of a white solid. 1H NMR (CDCl3), d (ppm): 1.91 (m, 2 H) 3.24 (m, 2 H) 4.13 (m, 2 H) 7.67 (m, 2 H) 8.65 (m, 2 H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with 3×10 ml chloroform
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef49bdf306a948179819227280b9be3a
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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