Isopropenyl chloroformate → Isopropenyl N-[4-bromo-2-fluoro-5-(7-methyl-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl)phenyl]carbamate

HRID 522734Notes

Reaction equation

HRID 522734 reaction equation
[Br:1][C:2]1[C:8]([C:9]2[C:20]([CH3:21])=[N:19][C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:7][C:5]([NH2:6])=[C:4]([F:22])[CH:3]=1.C([O-])(O)=O.[Na+].Cl[C:29]([O:31][C:32]([CH3:34])=[CH2:33])=[O:30]>CCOC(C)=O>[Br:1][C:2]1[C:8]([C:9]2[C:20]([CH3:21])=[N:19][C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:7][C:5]([NH:6][C:29](=[O:30])[O:31][C:32]([CH3:34])=[CH2:33])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 898141894-Bromo-2-fluoro-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)aniline

Product 1

HCID 89813406Isopropenyl N-[4-bromo-2-fluoro-5-(7-methyl-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-6-yl)phenyl]carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat a mixture of 4-bromo-2-fluoro-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)aniline (0.20 g, 0.527 mmol) in EtOAc (10 mL) and saturated. NaHCO3 (10 ml) with isopropenyl chloroformate (0.064 ml, 0.580 mmol) and stir the biphasic mixture vigorously at RT for 4 h. Separate the layers, extract the aqueous layer with additional EtOAc (1×), wash the combined organics with brine, dry over Na2SO4 and concentrate to dryness to afford the title compound (assume 100% yield). MS (m/z): 463.0.

Workup

  1. additionTreat
  2. customSeparate the layers
  3. extractionextract the aqueous layer with additional EtOAc (1×)
  4. washwash the combined organics with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-c22dd0fcca84494dbcb16cd060fc776e
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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