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

HRID 522728Notes

Reaction equation

HRID 522728 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[C:19]([CH3:20])=[N:18][C:11]3[N:12]=[C:13]([NH:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)[CH:7]=1.Cl[C:24]([O:26][C:27]([CH3:29])=[CH2:28])=[O:25]>N1C=CC=CC=1>[F:22][C:3]1[CH:4]=[C:5]([CH3:21])[C:6]([C:8]2[C:19]([CH3:20])=[N:18][C:11]3[N:12]=[C:13]([NH:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:7][C:2]=1[NH:1][C:24](=[O:25])[O:26][C:27]([CH3:29])=[CH2:28]

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 898135606-(5-Amino-4-fluoro-2-methylphenyl)-N,7-dimethylpyrido[2,3-d]pyrimidin-2-amine

Product 1

HCID 118048014Prop-1-en-2-yl (2-fluoro-4-methyl-5-(7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl)phenyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Treat a cooled solution (0° C.) of 6-(5-amino-4-fluoro-2-methylphenyl)-N,7-dimethylpyrido[2,3-d]pyrimidin-2-amine (0.85 g, 2.86 mmol) in pyridine (10 mL) dropwise with isopropenyl chloroformate (0.281 ml, 2.57 mmol) and stir the mixture for 20 min. at 0° C. Concentrate the mixture to dryness, dissolve the residue in DCM, wash with brine, dry over Na2SO4 and concentrate to dryness to afford the title compound. Use it without purification (assuming 100% yield). MS (m/z): 382.1 (M+1).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. dissolutiondissolve the residue in DCM
  3. washwash with brine
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-38ce905859d74b3baf6a9dc752227a7a
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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