Diisopropylethylamine → HCID 86657088, compound

HRID 2358997Notes

Reaction equation

HRID 2358997 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][C:13]=1[NH2:14].C(N(C(C)C)CC)(C)C>CC(O)C>[C:19]([C:16]1[CH:17]=[CH:18][C:12]([CH3:11])=[C:13]([NH:14][C:6]2[C:5]([O:9][CH3:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6014012,4-Dichloro-5-methoxypyrimidineHCID 130899795-tert-Butyl-2-methylaniline

Product 1

HCID 86657088HCID 86657088, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-5-methoxypyrimidine (200 mg, 1.12 mmol), 2-methyl-5-t-butylaniline (192 mg, 1.17 mmol) and diisopropylethylamine (1.5 mL) in 2-propanol (1.5 mL) was heated at 120° C. for 17 h in an oil bath. The mixture was cooled to room temperature and solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (Biotage system, EtOAc/Hexane, 0%-100%) to afford the product as a solid (166 mg, 48.6%).

Workup

  1. customsolvent was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (Biotage system, EtOAc/Hexane, 0%-100%)

Sources & evidence

ORD record
ord-112097aec7304dd3a930f7c71f0ad0e7
Source dataset
uspto-grants-2014_04
Patent number
US08685972B2

Reaction notes

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