5-Amino-2-chlorophenol → 2-Chloro-5-[(4-methoxypyrimidin-2-yl)amino]phenol

HRID 1474019Notes

Reaction equation

HRID 1474019 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:18])=[C:15]([OH:17])[CH:16]=1>CCO>[Cl:18][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=2)=[CH:16][C:15]=1[OH:17]

Participants

4

Reactant 2

HCID 806765-Amino-2-chlorophenolHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 684926902-Chloro-5-[(4-methoxypyrimidin-2-yl)amino]phenolYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Following the general procedure for the synthesis of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-chloro-4-methoxypyrimidine (87 mg, 0.60 mmol) and 5-amino-2-chlorophenol (86 mg, 0.60 mmol) in 10% aqueous EtOH (3 mL) was heated at 90° C. for 18 h. The title compound was obtained in 57% yield a (87 mg) and used for the next step without additional purification.

Sources & evidence

ORD record
ord-0d40beba1018496ca63c95161f36b5d9
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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