Diiodomethane → 2-[1-(2,3-Difluorobenzyl)-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 570549Notes

Reaction equation

N[C:2]1[C:3]2[C:29]([CH3:31])([CH3:30])[C:28](=[O:32])[NH:27][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13]([CH3:17])=[N:14][CH:15]=3)[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[N:9]=2)[N:7]=1.[I:33]CI.N(OCCC(C)C)=O.C(N(CC)CC)C>C(#N)C>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[C:11]2=[N:12][C:13]([CH3:17])=[N:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[C:2]([I:33])[C:3]3[C:29]([CH3:31])([CH3:30])[C:28](=[O:32])[NH:27][C:4]=3[N:5]=2)=[N:9]1

Participants

Conditions

Temperature: 85 °C

Procedure

150 mg (0.34 mmol) of 4-amino-2-[1-(2,3-difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were admixed with 6.650 g (19.86 mmol) of diiodomethane and 402 mg (3.44 mmol) of isopentyl nitrite. The mixture was stirred at 85° C. for 8 h. 70 mg (0.69 mmol) of triethylamine were added and the mixture was again boiled under reflux at 85° C. After cooling, the mixture was diluted with acetonitrile and purified by means of preparative HPLC (eluent: acetonitrile/water with, gradient 30:70→95:5). 44 mg (purity 67%, 16% of theory) of the target compound were obtained.

Workup

temperatureunder reflux at 85° C
temperatureAfter cooling
custompurified by means of preparative HPLC (eluent: acetonitrile/water with, gradient 30:70→95:5)
custom44 mg (purity 67%, 16% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-e25bc557b2dc483f929707dca3e0e09c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023849B2

Reaction notes

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