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2,6-Diaminopyridine → HCID 9926492, compound

HRID 568167
Notes
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Reaction equation

HRID 568167 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9](O[Si](C(C)(C)C)(C)C)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[N:27]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[NH2:32][C:28]1[N:27]=[C:26]2[C:31]([C:9]([C:10]3[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[NH:25]2)=[CH:30][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 521998p-Toluenesulfonic acid monohydrateHCID 10991586HCID 10991586, compound

Product 1

HCID 9926492HCID 9926492, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
135 °C

Procedure

1-(4-Fluorophenyl)-2-t-butyldimethylsiloxy-2-(4-pyridyl)ethanone (16) (3.45 g, 10.0 mmol), 2,6-diaminopyridine (1.09 g, 10.0 mmol), p-toluenesulfonic acid monohydrate (13.3 g, 70.0 mmol), and xylene (140 mL) were warmed to 60° C. under argon (note: all condensation reactions of this type were conducted behind an explosion shield). After 1 h at 60° C., the reaction was warmed to 135° C. for 3 h. After allowing the reaction to cool to 23° C., the top layer of xylene and p-toluenesulfonic acid was decanted from the bottom layer of gummy product residue. The lower product layer was partitioned between saturated bicarbonate (100 mL), and ethyl acetate (250 mL). The ethyl acetate layer was washed with brine (1×100 mL), and dried (Na2SO4). After concentration in vacuo, the residue was purified by applying flash chromatography (2 liters of ethyl acetate: hexane 7:3 followed by 100% ethyl acetate) to afford the cleanly separated regioisomer (17): Mass Spectrum (CI) 305 (MH+).

Workup

  1. customall condensation reactions of this type
  2. customthe reaction
  3. temperatureto cool to 23° C.
  4. customthe top layer of xylene and p-toluenesulfonic acid was decanted from the bottom layer of gummy product residue
  5. customThe lower product layer was partitioned between saturated bicarbonate (100 mL), and ethyl acetate (250 mL)
  6. washThe ethyl acetate layer was washed with brine (1×100 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationAfter concentration in vacuo
  9. customthe residue was purified

Sources & evidence

ORD record
ord-1af404de051749bda3439f320fb3c9fd
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06180643B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes