Acetone → 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

HRID 1677399Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.CO.CC(C)=O>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:38])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-Phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (405 mg, 1.05 mmol) and p-toluenesulfonic acid monohydrate (40 mg, 0.21 mmol) were placed in a 20 ml microwave vial with 14 ml of a 2:1 mixture of methanol and acetone. The reaction was heated in a microwave reactor at 100° C. for 1.5 hours. The reaction was diluted with ethyl acetate, washed two times with saturated sodium bicarbonate and water, dried and concentrated. The residue was triturated with ethyl acetate and hexanes, filtered, and dried to yield 175 mg of 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone. MS: (M+H)+=404. MP=226.0-227.0° C.

Workup

washwashed two times with saturated sodium bicarbonate and water
customdried
concentrationconcentrated
customThe residue was triturated with ethyl acetate and hexanes
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-cc30a89aa5a14234b1695b5f6d3c0b00
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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