Methyl iodide → 2-Amino-9-cyclopentyl-8-methyl-8,9-dihydro-7H-pyrido[3',2':4,5]pyrrolo[2,3-d]pyrimidin-7-one

HRID 79166Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]3[CH:11]=[CH:12][C:13]([OH:15])=[N:14][C:9]=3[N:8]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:7]=1.[H-].[Na+].IC.[C:25]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]3[CH:11]=[CH:12][C:13](=[O:15])[N:14]([CH3:25])[C:9]=3[N:8]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 272 (100 mg, 0.37 mmol) was dissolved in dry DMF (1 mL). Sodium hydride, 60% dispersion in oil (16.0 mg, 0.4 mmol) was added and the reaction stirred at 60° C. for 20 minutes. Iodomethane (26.5 μl, 423 μmol) was the added and the reaction stirred at 60° C. for 2 hr. The solution was allowed to cool and added to water (10 mLl) and aqueous K2CO3 (saturated, 2 mL), and extracted with ethyl acetate (2×30 mL), and dichloromethane+10% methanol (2×30 mLl). The combined organics were dried (MgSO4) and evaporated to give an orange solid. Silica gel chromatography (gradient elution hexanes+2.5% TEA/0-70% ethyl acetate+2.5% TEA) afforded compound 273 as a white solid, 64 mg (61%).

Workup

additionadded
stirringthe reaction stirred at 60° C. for 2 hr
temperatureto cool
extractionextracted with ethyl acetate (2×30 mL), and dichloromethane+10% methanol (2×30 mLl)
dry with materialThe combined organics were dried (MgSO4)
customevaporated
customto give an orange solid
washSilica gel chromatography (gradient elution hexanes+2.5% TEA/0-70% ethyl acetate+2.5% TEA)

Sources & evidence

ORD record: ord-907188c441614929a91a5b33a47bd71a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841312B2

Reaction notes

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