Isopropenyl chloroformate → Prop-1-en-2-yl (2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)carbamate

HRID 522721Notes

Reaction equation

HRID 522721 reaction equation
Cl[C:2]([O:4][C:5]([CH3:7])=[CH2:6])=[O:3].[F:8][C:9]1[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[C:28]([CH3:29])=[N:27][C:20]3[N:21]=[C:22]([S:25][CH3:26])[N:23]=[CH:24][C:19]=3[CH:18]=2)=[CH:12][C:10]=1[NH2:11]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:8][C:9]1[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[C:28]([CH3:29])=[N:27][C:20]3[N:21]=[C:22]([S:25][CH3:26])[N:23]=[CH:24][C:19]=3[CH:18]=2)=[CH:12][C:10]=1[NH:11][C:2](=[O:3])[O:4][C:5]([CH3:7])=[CH2:6]

Participants

5

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 898136922-Fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)benzenamine

Product 1

HCID 118048013Prop-1-en-2-yl (2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)carbamateYield 99.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add isopropenyl chloroformate (146 mg, 1.207 mmol) to a bi-phasic mixture of 2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)aniline (345 mg, 1.097 mmol) in EtOAc (15 mL) and saturated NaHCO3 (20 mL) and stir at RT for 2 h. Add EtOAc, separate the layers, wash the organic layer with brine, dry over Na2SO4 and concentrate to dryness to afford the title compound as an amorphous solid (434 mg, 99%). MS (m/z): 399.1 (M+1).

Workup

  1. customAdd EtOAc, separate the layers
  2. washwash the organic layer with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-3a254e2217054ae0881073a39938ca78
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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