5-Bromopyrimidine → 2-Fluoro-5-(5-pyrimidinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

HRID 419835Notes

Reaction equation

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

Participants

Reactant 2

HCID 783445-Bromopyrimidine

HCID 66651049HCID 66651049, compound

Product 1

HCID 666512152-Fluoro-5-(5-pyrimidinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Procedure

By carrying out the operation analogously to the first part of example 137, 5-(pinacolatoboryl)pyrimidine is prepared from 5-bromopyrimidine and is reacted immediately in the same reactor with 5-bromo-2-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation VIII, under conditions analogous to those applied in the preparation of example 177. The expected product is thus obtained in the form of a yellow solid (yield=40%).

Workup

customobtained
customthose applied in the preparation of example 177

Sources & evidence

ORD record: ord-bc436015f1ac4ac1a92102203a1bfd61
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093394B2

Reaction notes

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