P-Anisidine → HCID 53261253, compound

HRID 876155Notes

Reaction equation

HRID 876155 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[C:10](Cl)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([NH:5][C:6]1[CH:11]=[C:10]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 634876Binap, (A+-)-HCID 21749032N-tert-Butyl-6-chloropyrimidin-4-amine

Product 1

HCID 53261253HCID 53261253, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

50 mg of N-tert-butyl-6-chloropyrimidin-4-amine, 39 mg of p-anisidine, 104 mg of CsCO3, 1.2 mg of Pd(OAc)2 and 3 mg of BINAP were taken in a screw cap vial under argron in 2 mL of dry toluene and the vial obtained was kept in a heating block at 150° C. for 12 hours. The mixture obtained was cool to r.t. and purification was carried out by column chromatography using 30% EtOAc in PE. N4-tert-Butyl-N6-(4-methoxyphenyl)pyrimidine-4,6-diamine was obtained.

Workup

  1. customthe vial obtained
  2. customThe mixture obtained
  3. custompurification

Sources & evidence

ORD record
ord-7761375b39314659bdcab0bd71bf75b9
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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