Water → 2-Amino-4-chloro-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile

HRID 1356144Notes

Reaction equation

HRID 1356144 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([S:11]([CH3:13])=O)[N:3]=1.SC[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C1CCN2C(=NCCC2)CC1.O>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([S:11][CH2:13][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1509632-PyridineethanethiolHCID 185072772-Amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile

Product 1

HCID 185072462-Amino-4-chloro-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrileYield 22.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 1.00 g (4.62 mmol) 2-amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile in 10 ml DME were added 642 mg (4.62 mmol) 2-mercapto-ethylpyridine and 1.05 ml (6.92 mmol) DBU and stirring continued for 1 hour at room temperature. 50 ml water was then added and the resulting crystals collected by filtration and washed with ether. Chromatography (ethyl acetate/hexane 111 then ethyl acetate) followed by trituration in ether afforded 300 mg (22%) 2-amino-4-chloro-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 294 (M{37Cl}+H+, 30), 292 (M{35Cl}+H+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-bb9b4c41263f45409112e91f56a8b9da
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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