Bromoform → 4-bromo-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

HRID 2105143Notes

Reaction equation

N[C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1.C(Br)(Br)[Br:24].C(ON=O)CC(C)C>CS(C)=O>[Br:24][C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

The product of step (a) (0.5 g) was suspended in DMSO (10 ml) and bromoform (10 ml) and the mixture was heated to 125° C. Isoamylnitrite (2 ml) was added and the mixture was stirred at 125° C. for 5 minutes before being cooled in an ice bath. Solvent was removed by evaporation under high vacuum and the residue suspended in dichloromethane (100 ml). This suspension was washed with saturated aqueous ammonium chloride (50 ml) and then filtered through a plug of celite. The filtrate was evaporated and purified by column chromatography, eluting with 10% ethyl acetate in dichloromethane to give the subtitled compound as a white solid (0.22 g).

Workup

temperaturebefore being cooled in an ice bath
customSolvent was removed by evaporation under high vacuum
washThis suspension was washed with saturated aqueous ammonium chloride (50 ml)
filtrationfiltered through a plug of celite
customThe filtrate was evaporated
custompurified by column chromatography
washeluting with 10% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-c578947adf6144f8af2c6b1852c52e7a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579342B2

Reaction notes

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