Ethanol → HCID 69782329, compound

HRID 1356136Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10](Br)=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH2:44]([OH:46])[CH3:45].CN([CH:50]=[O:51])C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:44]([O:46][C:50]([C:10]1[O:9][C:8]([C:6]2[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:12][CH:11]=1)=[O:51])[CH3:45]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 1.17 g (3.74 mmol) 2-amino-4-(5-bromo-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 15 ml DMF at room temperature were added 343 mg (0.37 mmol) tris(dibenzylideneacetone)dipalladium(O) and 287 mg (0.94 mmol) triphenylarsine. Carbon monoxide was bubbled through the reaction mixture for 10 min, then 2.61 ml (18.7 mmol) triethylamine and 10.9 ml (187 mmol) ethanol were added. The reaction mixture was then heated at 90° C. for 16 hours under a carbon monoxide atmosphere (balloon). The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane then ethyl acetate) afforded 70 mg (6%) 5-(2-amino-5-cyano-6-methylsulfanyl-pyrimidin-4-yl)-furan-2-carboxylic acid ethyl ester as a yellow crystalline solid. EI-MS m/e (%): 304 (M+, 95), 303 ([M—H]+, 100), 275 (32), 259 (93), 231 (72), 202 (32).

Workup

customCarbon monoxide was bubbled through the reaction mixture for 10 min
concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-09ab6acda29d48aeb852d3a6588a2ac6
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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