Tetrahydrofuran → HCID 59553878, compound

HRID 1170925Notes

Reaction equation

HRID 1170925 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:17](=[O:26])[C:18]2[C:24](Cl)=[N:23][CH:22]=[CH:21][C:19]=2[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1C[O:40][CH2:39]C1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:17](=[O:26])[C:18]2[C:24]([O:40][CH3:39])=[N:23][CH:22]=[CH:21][C:19]=2[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 59553892HCID 59553892, compound

Product 1

HCID 59553878HCID 59553878, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(2-benzyloxy-phenyl)-5-chloro-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one, sodium hydride (60% suspension in mineral oil) (1.5 equiv.), and corresponding alcohol (1.5 equiv.) in THF was heated at 70° C. overnight. The reaction was cooled to RT, solvent removed, water and ethyl acetate were added and phases separated. The aqueous phase was washed with ethyl acetate (2×), organic portions combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified on preparative TLC plate using 1:1 ethyl acetate:heptane.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customsolvent removed
  3. additionwater and ethyl acetate were added
  4. customphases separated
  5. washThe aqueous phase was washed with ethyl acetate (2×), organic portions
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on preparative TLC plate

Sources & evidence

ORD record
ord-c57c996d14ed4640af2fcfc8178e47dd
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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