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

HRID 1356143Notes

Reaction equation

HRID 1356143 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([S:11]([CH3:13])=O)[N:3]=1.[SH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[CH2:23]1[CH2:33][CH2:32][N:31]2[C:26](=NCCC2)[CH2:25][CH2:24]1.O>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([S:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH2:13][CH2:25][C:26]2[CH:24]=[CH:23][CH:33]=[CH:32][N:31]=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 185074362-Amino-4,6-bis-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrileYield 33%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 500 mg (2.31 mmol) 2-amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile in 10 ml DME were added 482 mg (3.46 mmol) 2-mercapto-ethylpyridine and 0.88 ml (5.77 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 ethyl acetate to afford 300 mg (33%) 2-amino-4,6-bis-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 395 (M+H+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-c8c938cb5e3f4a3ba69378c1d2ce005b
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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