tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 131717243, compound

HRID 1729406Notes

Reaction equation

HRID 1729406 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][C:5]([CH2:11][CH2:12][CH2:13][CH3:14])=[N:6]2.[C:15]([O:19][C:20]([C:22]1[C:23]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=2)=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[CH2:11]([C:5]1[N:6]([CH2:34][C:31]2[CH:32]=[CH:33][C:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[CH:29][CH:30]=2)[C:7]2[C:3]([N:4]=1)=[C:2]([Cl:1])[N:10]=[CH:9][N:8]=2)[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 19012216HCID 19012216, compound

Product 1

HCID 131717243HCID 131717243, compound

Procedure

The titled compound was prepared by the alkylation of 6-chloro-8-butyl purine (0.063 g, 0.3 mmol) with t-Butyl-4-bromomethylbiphenyl-2'-carboxylate (0.104 g, 0.3 mmol) according to the procedure described in Step 3 of Example 12. After flash-chromatographic purification of the crude product using ethyl acetate-hexane (1:1), the product was obtained as a foam (0.085 g, 60%). NMR (CDCl3): δ 0.946 (t, J=9Hz, 3H), 1.26 (s, 9H), 1.464 (m, 2H), 1.86 (m, 2H), 2.91 (m, 2H), 5.51 (s, 2H), 7.16-7.51 (m, 7H), 7.78 (m, 1H) and 8.723 (s, 1H). FAB-MS: m/e 477 and 479 (M+H).

Workup

  1. customAfter flash-chromatographic purification of the crude product

Sources & evidence

ORD record
ord-7523e2f861fe4677884207aa94d0ed6c
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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