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

HRID 1010977Notes

Reaction equation

[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)=[C:9]([NH2:22])[N:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:30])C(=O)C1>C(Cl)(Cl)Cl>[Br:30][C:12]1[N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:14]2[C:10]([N:11]=1)=[C:9]([NH2:22])[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]1[CH2:2][CH2:3]1)[N:15]=2

Participants

Conditions

Temperature: 1 °C

Procedure

2-[(2-Cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.579 g) was dissolved in chloroform (15 mL) and was cooled in an ice bath to 1° C. NBS (1.02 g) was added gradually, keeping the reaction temperature below 2° C. The reaction was stirred for 30 mins (with cooling in an ice bath) before being allowed to warm to room temperature. The reaction was then stirred for 6 h. Chloroform (50 mL) was added and the mixture was partitioned with water (50 mL) and was separated using a hydrophobic frit. The organics were evaporated under reduced pressure to give the title compound as a brown foam (1.867 g).

Workup

customthe reaction temperature below 2° C
temperature(with cooling in an ice bath)
temperatureto warm to room temperature
stirringThe reaction was then stirred for 6 h
customthe mixture was partitioned with water (50 mL)
customwas separated
customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record: ord-4f9cd807e1cc4a0ea47bc87de4fe92d8
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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