Butyl bromide → 2-(9-butyl-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol

HRID 2093388Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])[NH:8]2)=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.Br[CH2:22][CH2:23][CH2:24][CH3:25]>>[CH2:22]([N:8]1[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[CH2:23][CH2:24][CH3:25]

Participants

Reactant 2

HCID 8002Butyl bromide

HCID 178458928HCID 178458928, compound

Product 1

HCID 580152122-(9-butyl-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol

Procedure

2-(2-Chloro-6-morpholino-9H-purin-8-yl)propan-2-ol 100 mg was treated with bromobutane via General Procedure C to give crude intermediate 2-(9-butyl-2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol which was treated with 2-aminopyrimidine-5-boronic acid, pinacol ester via General Procedure A and was purified via reverse phase HPLC to give 55 mg of 103 as a white solid. MS (Q1) 413.3 (M)+.

Sources & evidence

ORD record: ord-741a1f1cbb05426db1a45598879ce6d2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445487B2

Reaction notes

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