1,1-Dimethoxyethane → HCID 18328131, compound

HRID 1921910Notes

Reaction equation

HRID 1921910 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.COC(OC)C.[CH2:17]1[CH2:27]CN2C(=NCCC2)[CH2:19][CH2:18]1>CN(C=O)C>[CH3:19][C:18]1[CH:17]=[CH:27][N:10]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 107951,1-DimethoxyethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2776844Pyridine-4-amidine hydrochloride

Product 1

HCID 18328131HCID 18328131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Isonicotinamidine hydrochloride (5.00 g, 31.7 mmol) and acetaldehyde dimethylacetal (8.44 mL, 63.5 mmol) were combined and heated to 110° C. in anhydrous DMF (35 mL) in the presence of DBU (14.20 mL, 95.2 mmol) for 3 h. The reaction mixture was cooled to 20° C., then stirred for 16 h, before being concentrated in vacuo. The residue was partitioned between H2O (100 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2×50 mL), then the combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Flash column chromatography (EtOAc) of the residue gave 4-methyl-2-pyridin-4-yl-pyrimidine: δH ((CD3)2SO): 2.57 (3H, s), 7.45 (1H, d), 8.21-8.26 (2H, m), 8.72-8.77 (2H, m), 8.82 (1H, d). To a solution of this compound (1.06 g, 6.17 mmol) in anhydrous dioxane (20 mL) was added SeO2 (2.05 g, 18.51 mol), then the mixture was heated to reflux for 90 h. The reaction mixture was cooled to 20° C. then filtered, washing with EtOAc. The filtrate was evaporated to dryness, then the residue was suspended in CH2Cl2. The suspension was filtered, washing with CH2Cl2, then the filtrate was evaporated to dryness to furnish the title compound: δH (CDCl3): 7.80 (1H, d), 8.38 (2H, d), 8.83 (2H, d), 9.13 (1H, d), 10.15 (1H, s).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe residue was partitioned between H2O (100 mL) and EtOAc (100 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washthe combined organics were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2f958a952b945efa5172a7b51d2ee0b
Source dataset
uspto-grants-2012_05
Patent number
US08173807B2

Reaction notes

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