2,6-Diaminopyridine → HCID 54266633, compound

HRID 2420099Notes

Reaction equation

HRID 2420099 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[N:19]=1>N1C=CC=CC=1>[NH2:17][C:18]1[N:19]=[C:20]([N:24]=[C:4]2[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]2)[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 88612,6-DiaminopyridineHCID 12874874HCID 12874874, compound

Product 1

HCID 54266633HCID 54266633, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (20 g) is added in small portions to a solution of 2,6-diaminopyridine (60 g) in pyridine (400 cc). The suspension passes rapidly into solution. After 15 hours at a temperature of about 20° C the solution is concentrated to dryness under reduced pressure (25 mm Hg). The residue is taken up in methylene chloride (500 cc); the insoluble material (47 g) consists of 2,6-diaminopyridine. The methylene chloride solution is washed with water (3 × 100 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (20 mm Hg). After addition to the residue obtained of a mixture (250 cc) of water and ethanol (4:1 by volume) the mixture is heated to the boiling point. After cooling to 5° C the resulting crystals are filtered off and washed with ethanol (50 cc) to give (S)-3-[(6-aminopyrid-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (11 g) in the form of white crystals melting at 128° C.

Workup

  1. concentrationAfter 15 hours at a temperature of about 20° C the solution is concentrated to dryness under reduced pressure (25 mm Hg)
  2. washThe methylene chloride solution is washed with water (3 × 100 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  6. additionAfter addition to the residue
  7. customobtained of a mixture (250 cc) of water and ethanol (4:1 by volume) the mixture
  8. temperatureis heated to the boiling point
  9. filtrationare filtered off
  10. washwashed with ethanol (50 cc)

Sources & evidence

ORD record
ord-2d6e67ef427944b29a7ecdbdbfba3a9b
Source dataset
uspto-grants-1978_08
Patent number
US04108999

Reaction notes

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