1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Ethyl-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-ylamine

HRID 1356036Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[N:5][C:6]([NH2:12])=[N:7][C:8]=1[S:9]([CH3:11])=O)[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]CS.C1CCN2C(=NCCC2)CC1>COCCOC>[CH2:1]([C:3]1[C:4]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[N:5][C:6]([NH2:12])=[N:7][C:8]=1[S:9][CH2:11][CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred suspension of 100 mg (0.40 mmol) 5-ethyl-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine in 5 ml DME in a pressure tube were added 230 mg (1.65 mmol) 2-pyridylethyl mercaptan and 0.18 ml (1.19 mmol) DBU and the mixture heated at 90° C. for 16 hours. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/1 then ethyl acetate) followed by trituration in ether afforded 25 mg (19%) 5-ethyl-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-ylamine as a beige crystalline solid. ES-MS m/e (%): 327 (M+H+, 100).

Workup

concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-ef7600991f25445d97fcf284a44f807f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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