3-(Methylthio)-1-propanol → HCID 59639530, compound

HRID 2357274Notes

Reaction equation

HRID 2357274 reaction equation
[H-].[Na+].[CH3:3][S:4][CH2:5][CH2:6][CH2:7][OH:8].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[N:17]1[C:22]2[N:23]=[C:24](S(C)(=O)=O)[N:25]=[C:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[CH3:34])[C:21]=2[CH:20]=[CH:19][C:18]1=[O:39]>>[F:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[C:11]=1[N:17]1[C:22]2[N:23]=[C:24]([O:8][CH2:7][CH2:6][CH2:5][S:4][CH3:3])[N:25]=[C:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[CH3:34])[C:21]=2[CH:20]=[CH:19][C:18]1=[O:39]

Participants

4

Reactant 3

HCID 104483-(Methylthio)-1-propanolHCID 24758Sodium hydrideHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 59639530HCID 59639530, compound

Procedure

NaH (12 mg, 0.5 mmol) was added to 3-(methylthio)-1-propanol (0.5 mL) and the mixture was stirred under Ar at 230. After 5 min, gas evolution ceased, and the product of Example 48 (223 mg, 0.5 mmol) was added in a single portion. The mixture was stirred for 30 minutes. Most of the excess 3-(methylthio)-1-propanol was removed in vacuo, and the residue partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography eluted with 10-30% EtOAc/hexane, followed by recrystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. mp 127-128°, LC MS m/z=472 (MH+) Retention time=2.47 min.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customMost of the excess 3-(methylthio)-1-propanol was removed in vacuo
  3. customthe residue partitioned between EtOAc and H2O
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over anhyd Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product
  9. washFlash chromatography eluted with 10-30% EtOAc/hexane
  10. customfollowed by recrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-eccb23feb1214ad4a6bde2886442ef1d
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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