tert-Butyl [2-({3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethynyl)pyridin-4-yl]carbamate → tert-Butyl [2-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-4-yl]carbamate

HRID 541839Notes

Reaction equation

HRID 541839 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([C:15]#[C:16][C:17]3[CH:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:19][N:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:31])=[CH:4][N:3]=1>CO.O1CCCC1.[Pd]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]3[CH:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:20]=[CH:19][N:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:31])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 57962565tert-Butyl [2-({3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethynyl)pyridin-4-yl]carbamate

Product 1

HCID 57961542tert-Butyl [2-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-4-yl]carbamateYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl [2-({3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethynyl)pyridin-4-yl]carbamate (740 mg, 1.6 mmol) in methanol (15 mL) and tetrahydrofuran (15 mL) was added 10% palladium on carbon (148 mg, 0.139 mmol). The resultant mixture was hydrogenated at 55 psi for 20 hours. The crude mixture was filtered and concentrated to give the desired product as a light yellow solid (0.65 g, 87%). LCMS for C22H24Cl2N5O2 (M+H)+: m/z=460.0, 462.0.

Workup

  1. filtrationThe crude mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-af9f2bf6dcb44190922863fc62a08cc9
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…