Water → 2-Amino-4-methylsulfanyl-6-phenoxy-pyrimidine-5-carbonitrile

HRID 1356150Notes

Reaction equation

HRID 1356150 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1CCN2C(=NCCC2)CC1.O>COCCOC>[NH2:1][C:2]1[N:3]=[C:4]([S:11][CH3:12])[C:5]([C:9]#[N:10])=[C:6]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 185073912-Amino-4-methylsulfanyl-6-phenoxy-pyrimidine-5-carbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 500 mg (2.04 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 5 ml DME were added 192 mg (2.04 mmol) phenol and 0.31 ml (2.04 mmol) DBU and stirring continued for 16 hours at room temperature. 15 ml water was then added and the resulting crystals collected by filtration and triturated in hexane to afforded 400 mg (76%) 2-amino-4-methylsulfanyl-6-phenoxy-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 258 (M+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. customtriturated in hexane

Sources & evidence

ORD record
ord-130cabeb29584e79b5fc4fbb2a04ee7f
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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