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4-Toluenesulfonyl chloride → 1-(2-Fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzene sulfonate

HRID 1487152
Notes
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Reaction equation

HRID 1487152 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2[N:15]([CH3:22])[C:16](=[O:21])[C:17]([CH3:20])=[C:18]([OH:19])[C:13]=2[C:12](=[O:23])[N:11]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:10]1=[O:33].C(N(CC)CC)C.Cl.CN(C)C.[C:46]1([CH3:56])[CH:51]=[CH:50][C:49]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:47]=1>C(#N)C.CO>[CH3:56][C:46]1[CH:51]=[CH:50][C:49]([S:52]([O:19][C:18]2[C:13]3[C:12](=[O:23])[N:11]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)[C:10](=[O:33])[N:9]([C:3]4[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=4[F:1])[C:14]=3[N:15]([CH3:22])[C:16](=[O:21])[C:17]=2[CH3:20])(=[O:54])=[O:53])=[CH:48][CH:47]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 597173301-(2-fluoro-4-iodophenyl)-5-hydroxy-3-(4-methoxybenzyl)-6,8-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

Product 1

HCID 89815880
1-(2-Fluoro-4-iodophenyl)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzene sulfonate
Yield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

Under nitrogen atmosphere, to a solution of 1-(2-fluoro-4-iodophenyl)-5-hydroxy-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (41 g, 72.8 mmol) (Prepared as per reference WO2005121142) in acetonitrile (300 ml), triethylamine (30.4 ml, 218 mmol) and trimethylamine hydrochloride (3.48 g, 36.4 mmol) were added slowly followed by addition of p-toluensulfonylchloride (27.8 g, 146 mmol) in acetonitrile (300 ml) at 0° C., and the mixture was stirred under ice cooling for 1 hr, and then at room temperature for 24 h. To the reaction mixture was added methanol (220 ml), and the mixture was stirred at room temperature for 1 h. The precipitated crystals were collected by filtration, dried under vacuum to afford the titled compound (40.5 g, 78%)

Workup

  1. waitat room temperature for 24 h
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-574e86b4cab14ebab84ce411b7d1c5fa
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428499B2

Reaction notes

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