Sodium hydride → HCID 59639605, compound

HRID 2249793Notes

Reaction equation

HRID 2249793 reaction equation
[CH2:1]1[O:6]C(C2C=CC=CC=2)[O:4][CH2:3][CH:2]1[OH:13].[H-].[Na+].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[N:24]1[C:29]2[N:30]=[C:31](S(C)(=O)=O)[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[CH3:41])[C:28]=2[CH:27]=[CH:26][C:25]1=[O:46]>C1COCC1>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[N:24]1[C:29]2[N:30]=[C:31]([O:13][CH:2]([CH2:3][OH:4])[CH2:1][OH:6])[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[CH3:41])[C:28]=2[CH:27]=[CH:26][C:25]1=[O:46]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 59639605HCID 59639605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

1,3-O-Benzylideneglycerol (100 mg, 0.55 mmol) was dissolved in dry THF (5 mL) and stirred under Ar at 23° C. NaH (14 mg, 0.55 mmol) was added and the mixture stirred for 15 minutes at 23° C., and then cooled to −78°. The product of Example 48 (222 mg, 0.5 mmol) was added, and the mixture was allowed to slowly warm to 23°. The solvent was removed in vacuo, and the residue was dissolved in acetic acid (2 mL), and H2O (0.5 mL) was added. The mixture was heated in an oil bath to 60° C. for three h, and then the solvents were removed in vacuo to give the crude product. The crude product was flash chromatographed twice on silica gel eluted with 20-50% EtOAc/CH2Cl2 to give the product as a white-amorphous solid. 104-107° C., LC MS m/z=458 (MH+) Retention time=1.88 min.

Workup

  1. stirringthe mixture stirred for 15 minutes at 23° C.
  2. temperaturecooled to −78°
  3. temperatureto slowly warm to 23°
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in acetic acid (2 mL)
  6. additionH2O (0.5 mL) was added
  7. temperatureThe mixture was heated in an oil bath to 60° C. for three h
  8. customthe solvents were removed in vacuo
  9. customto give the crude product
  10. customchromatographed twice on silica gel
  11. washeluted with 20-50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-aef9971f89d5401795e9edf4026203f1
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

Loading…