Water → 2-Amino-4-methylsulfanyl-6-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile

HRID 1356146Notes

Reaction equation

HRID 1356146 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.[OH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=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:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 185072202-Amino-4-methylsulfanyl-6-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrileYield 16.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 1.00 g (4.08 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml DME were added 0.33 ml (4.08 mmol) 2-(hydroxymethyl)pyridine and 0.62 ml (4.08 mmol) DBU and stirring continued for 16 hours at room temperature. 50 ml water was then added and the resulting crystals collected by filtration. Chromatography (ethyl acetate) followed by trituration in ether afforded 180 mg (16%) 2-amino-4-methylsulfanyl-6-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 273 (M+, 100), 258 (89), 108 (63), 92 (95), 65 (70), 39 (36).

Workup

  1. filtrationthe resulting crystals collected by filtration

Sources & evidence

ORD record
ord-dcd73f3446154569b9a26a274ecb32c5
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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