5-Bromo-2-iodopyrimidine → HCID 123726157, compound

HRID 1485638Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[N:25]=[C:24]([O:26][C@H:27]3[C@H:31]4[O:32][CH2:33][C@@H:34]([OH:35])[C@H:30]4[O:29][CH2:28]3)[N:23]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=1.[Br:44][C:45]1[CH:46]=[N:47][C:48](I)=[N:49][CH:50]=1>>[Br:44][C:45]1[CH:46]=[N:47][C:48]([C:11]2[CH:10]=[CH:9][C:8]([C:7]3[N:6]=[C:5]4[N:23]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:43])[CH3:42])[C:24]([O:26][C@H:27]5[C@H:31]6[O:32][CH2:33][C@@H:34]([OH:35])[C@H:30]6[O:29][CH2:28]5)=[N:25][C:4]4=[CH:3][C:2]=3[Cl:1])=[CH:13][CH:12]=2)=[N:49][CH:50]=1

Participants

Reactant 2

HCID 70066515-Bromo-2-iodopyrimidine

HCID 123678375(3R,3aR,6R,6aR)-6-(6-Chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 123726157HCID 123726157, compound

Procedure

The title compound is prepared from (3R,3aR,6R,6aR)-6-(6-chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol and 5-bromo-2-iodopyrimidine following a procedure analogous to that described for Intermediate 3 (Step 3). LC (method 1): tR=1.28 min; Mass spectrum (ESI+): m/z=660, 662 [M+H]+.

Sources & evidence

ORD record: ord-aa2a24d6c8ac4d6b90e6d4f04621978b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422312B2

Reaction notes

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