Triethylamine → HCID 178496589, compound

HRID 641678Notes

Reaction equation

HRID 641678 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([O:15][CH3:16])[CH2:11][CH2:10]2)[C:5](/[CH:17]=[CH:18]/[C:19](OCC)=[O:20])=[C:4]([CH3:24])[N:3]=1.CCCCC=CCCCCC.C(N(CC)CC)C>COC(C)(C)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[C:5]2[CH:17]=[CH:18][C:19](=[O:20])[N:8]([C@H:9]3[CH2:14][CH2:13][C@H:12]([O:15][CH3:16])[CH2:11][CH2:10]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1365885-UndeceneHCID 178471089HCID 178471089, compound

Product 1

HCID 178496589HCID 178496589, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of (E)-ethyl 3-(2-amino-4-(trans-4-methoxycyclohexylamino)-6-methylpyrimidin-5-yl)acrylate (674 mg, 2.02 mmol) thiophenol (621 ul, 6.05 mmol), 1,5-diazabicyclo5,4,0)undec-5-ene (1.81 mL, 12.1 mmol) and triethylamine (1.69 mL, 12.1 mmol) in N′,N-dimethylformamide (15 mL) was heated in the microwave for 30 minutes at 100° C. then in an oil bath at 100° C. overnight. The reaction mixture was diluted with methyltertbutylether and washed with saturated sodium carbonate, brine, 0.1 N hydrochloric acid, brine, dried (MgSO4), filtered and concentrated. The combined aqueous layer was extracted with dichloromethane (2×). The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/methanol (0-5%) to afford 2-amino-8-(trans-4-methoxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (482 mg, 83%).

Workup

  1. customat 100° C.
  2. customovernight
  3. washwashed with saturated sodium carbonate, brine, 0.1 N hydrochloric acid, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. extractionThe combined aqueous layer was extracted with dichloromethane (2×)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash chromatography
  12. washeluting with chloroform/methanol (0-5%)

Sources & evidence

ORD record
ord-bdfcc1a54730406495d90f81dfdd0e97
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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