Water → HCID 57699806, compound

HRID 1011018Notes

Reaction equation

[CH:1]1([CH2:7][O:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][N:15]3[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:11]([NH2:24])[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:25]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Br:25][C:14]1[N:15]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:16]2[C:12]([N:13]=1)=[C:11]([NH2:24])[N:10]=[C:9]([O:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[N:17]=2

Participants

Conditions

Temperature: 2 °C

Procedure

2-[(Cyclohexylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.0364 g) was dissolved in chloroform (20 mL) and cooled to 0° C. before N-bromosuccinimide (0.5852 g) was added gradually (the reaction temperature not exceeding 1.9° C. during the addition of N-bromosuccinimide). The reaction mixture was stirred at ˜2° C. for 15 minutes before being warmed to room temperature at which it was stirred for 6 hours (under nitrogen). Water (100 mL) was added to the reaction mixture and stirred rapidly before the organic layer was separated using a hydrophobic frit. The organic phase was evaporated under reduced pressure to give dark brown oil. This material was purified by silica chromatography eluting with 0-50% ethyl acetate; cyclohexane to give the title compound as a pale yellow solid (0.8200 g).

Workup

additionwas added gradually (the reaction temperature not
temperaturebefore being warmed to room temperature at which it
stirringwas stirred for 6 hours (under nitrogen)
stirringstirred rapidly before the organic layer
customwas separated
customThe organic phase was evaporated under reduced pressure
customto give dark brown oil
customThis material was purified by silica chromatography
washeluting with 0-50% ethyl acetate

Sources & evidence

ORD record: ord-4eb6c3cab08f4140849f343f01344fab
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

Loading…