Diiodomethane → 2-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 536502Notes

Reaction equation

I[CH2:2][I:3].N(OCCC(C)C)=O.NC1[C:14]2[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:15]=2[N:16]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][C:24]([CH3:28])=[N:25][CH:26]=3)[N:21]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[N:20]=2)[N:18]=1>C(#N)C>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][N:21]1[C:22]2=[N:23][C:24]([CH3:28])=[N:25][CH:26]=[C:27]2[C:19]([C:17]2[N:18]=[C:2]([I:3])[C:14]3[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:15]=3[N:16]=2)=[N:20]1

Participants

Conditions

Temperature: 85 °C

Procedure

3.770 g (14.08 mmol) of diiodomethane and 411 mg (3.51 mmol) of isopentyl nitrite were added to 70 mg (0.17 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one. The mixture was stirred for 8 h at 85° C. After cooling, it was diluted with acetonitrile and the mixture was purified by preparative HPLC (eluent: acetonitrile/water, gradient 30:70→95:5). 35 mg (24% of theor.) of the target compound was obtained.

Workup

temperatureAfter cooling
customthe mixture was purified by preparative HPLC (eluent: acetonitrile/water, gradient 30:70→95:5)
custom35 mg (24% of theor.) of the target compound was obtained

Sources & evidence

ORD record: ord-a99bf0aaad294b9abfea942c28c1b8c0
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859569B2

Reaction notes

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