2-(Tributylstannyl)pyrimidine → 1-(beta-D-glucopyranosyl)-4-methyl-3-(5-(2-pyrimidinyl)-2-thienylmethyl)benzene

HRID 549975Notes

Reaction equation

HRID 549975 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]2[S:33][C:34](Br)=[CH:35][CH:36]=2)[CH:25]=1)(=O)C.C([Sn](CCCC)(CCCC)[C:43]1[N:48]=[CH:47][CH:46]=[CH:45][N:44]=1)CCC>>[C@@H:6]1([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]3[S:33][C:34]([C:43]4[N:48]=[CH:47][CH:46]=[CH:45][N:44]=4)=[CH:35][CH:36]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

3

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 666079031-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5-bromo-2-thienylmethyl)-4-methylbenzene

Product 1

HCID 113049221-(beta-D-glucopyranosyl)-4-methyl-3-(5-(2-pyrimidinyl)-2-thienylmethyl)benzene

Procedure

1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-bromo-2-thienylmethyl)-4-methylbenzene obtained in Example 159-(1) and tri-n-butyl(2-pyrimidinyl)tin 54 were treated in a manner similar to Example 128-(5) and (6) to give the target compound. APCI-Mass m/Z 429 (M+H).

Workup

  1. customto give the target compound

Sources & evidence

ORD record
ord-641a4823c3ac4fd581b4b844d7e31b59
Source dataset
uspto-grants-2011_05
Patent number
US07943788B2

Reaction notes

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