Dichloromethane → (R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2223146Notes

Reaction equation

HRID 2223146 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:10]1[N:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=2)[C:12](=[O:23])[C:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20](=[O:22])[CH3:21])[C:14]=2[N:15]=1)[CH3:9])(C)(C)C.ClCCl>FC(F)(F)C(O)=O>[C:20]([N:16]1[C:14]2[N:15]=[C:10]([C@H:8]([NH2:7])[CH3:9])[N:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=3)[C:12](=[O:23])[C:13]=2[CH2:19][CH2:18][CH2:17]1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 58617397(R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 58617407(R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

D3 (268 mg, 0.59 mmol) was dissolved in 1:1 trifluoroacetic acid:dichloromethane (10 mL). The reaction stirred at room temperature for 30 min. The solvent was removed in vacuo, then 10% aqueous ammonium hydroxide was added until the aqueous pH=9. The aqueous layer was extracted three times with dichloromethane, then the combined organic layer was washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, and concentrated in vacuo, recovering 170 mg of D4. MS (MH+): 357.1. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.13 (ddd, 2H, J=18.9, 1.4, 1.1 Hz), 7.02 (ddd, 2H, J=9.0, 1.2, 0.8 Hz), 4.09 (dq, 2H, J=6.9, 1.2 Hz), 3.98-3.80 (ddq, 2H, J=62.6, 5.3, 1.0 Hz), 3.73 (dd, 1H, J=6.6, 1.2 Hz), 2.60 (s, 3H), 1.92 (m, 2H), 1.82 (broad s, 2H), 1.45 (ddd, 3H, J=8.3, 6.1, 1.3 Hz), 1.28-1.21 (m, 5H) ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. addition10% aqueous ammonium hydroxide was added until the aqueous pH=9
  3. extractionThe aqueous layer was extracted three times with dichloromethane
  4. washthe combined organic layer was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialIt was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customrecovering 170 mg of D4

Sources & evidence

ORD record
ord-63b4fc9a6f684159bc2557e5bb0040df
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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