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Water → HCID 10111115, compound

HRID 556578
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Reaction equation

HRID 556578 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].CS([C:12]1[N:13]=[C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:15]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[N:17]=1)(=O)=O.O>CN(C=O)C>[O:22]=[C:19]1[N:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[N:17]=[C:12]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:13]=[C:14]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:15]=2[CH:21]=[CH:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 59639663HCID 59639663, compound

Product 1

HCID 10111115HCID 10111115, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To a solution of methylsulfonamide (200 mg, 2 mmol, 4 eq) in DMF (2 mL) was added NaH (80 mg, 2 mmol, 60% dispersion in mineral oil, 4 eq) and the reaction mixture was stirred for 30 min at 23°. To this solution was added a solution of 2-methanesulfonyl-4,8-diphenyl-8H -pyrido[2,3-d]pyrimidin-7-one (190 mg, 0.5 mmol) in DMF (1 mL) and the mixture was heated to 50°. After 1 h, H2O (10 mL) was added and then Et2O (10 mL), the layers were separated, and the organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and the solvent was evaporated. The yellow residue was then purified by Flash chromatography to afford N-(7-oxo-4,8-diphenyl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-methanesulfonamide (101 mg, 51% yield). 1H-NMR (CDCl3) δ 2.82 (s, 3H), 6.69 (d, 1H, J=9.8 Hz), 7.31 (m, 2H), 7.59 (m, 8H), 7.91 (d, 1H, J=9.8 Hz), LC MS (m/e)=393 (MH+).

Workup

  1. temperaturethe mixture was heated to 50°
  2. waitAfter 1 h
  3. customEt2O (10 mL), the layers were separated
  4. washthe organic layer was washed with satd aq NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe yellow residue was then purified by Flash chromatography

Sources & evidence

ORD record
ord-8bdd9f85f2304effa1535db9824791bc
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058282B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes