N-bromobutanimide → 8-Bromo-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

HRID 1011030Notes

Reaction equation

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

Participants

Conditions

Temperature: 1 °C

Procedure

2-[(Tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.7202 g) was dissolved in chloroform (15 mL) and cooled to ˜1° C. before N-bromosuccinimide (1.056 g) was added keeping the reaction temperature below 2° C. The reaction mixture was then stirred at ˜1° C. for 30 minutes before allowing to warm to room temperature were upon the reaction mixture was stirred for 3 hours. The reaction mixture was then stood overnight at room temperature before being partitioned between water (50 mL) and the organic phase separated using a hydrophobic frit. The organic phase was evaporated under reduced pressure to give a brown gum which was purified using silica chromatography (ISCO) eluting with 0-100% ethyl acetate: cyclohexane. This gave the title compound as a white foam solid (1.3748 g).

Workup

additionwas added
customthe reaction temperature below 2° C
temperatureto warm to room temperature
stirringwas stirred for 3 hours
waitThe reaction mixture was then stood overnight at room temperature
custombefore being partitioned between water (50 mL)
customthe organic phase separated
customThe organic phase was evaporated under reduced pressure
customto give a brown gum which
customwas purified
washeluting with 0-100% ethyl acetate

Sources & evidence

ORD record: ord-acb95e2d63334859858c8f37aed83801
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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