Sodium Carbonate → HCID 136217478, compound

HRID 1752428Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A 100 mL round-bottom flask was charged with 4-hydroxyphenyl boronic acid (1 g, 7.25 mmol), 6-((S)-1-carbamoyl-ethylamino)-2-chloro-pyrimidine-4-carboxylic acid amide (7.25 mmol, 1.76 g), PdCl2(PPh3)2 (Aldrich, 0.5 mmol, 0.3562 g), Na2CO3 (7.25 mL, 2M aqueous solution), and dioxane (5 mL). The flask was purged with nitrogen and heated to 100° C. for 16 h at which time the reaction was complete. The reaction mixture was concentrated under reduced pressure. The residue was suspended in 50% MeOH in DCM, filtered by vacuum, and the filter cake was discarded. The filtrate was concentrated under reduced pressure and was suspended in DCM, stirred for one hour, and filtered by vacuum filtration to provide the title compound as a light brown powder (2 g, 91%). 1H NMR (CD3OD) 8.25-8.09 (m, 2H), 7.09-6.92 (m, 1H), 6.82-6.70 (m, 2H), 4.62-4.40 (m, 1H), 1.49-1.31 (m, 3H). LC/MS: m/z 301[M+H]+.

Workup

customThe flask was purged with nitrogen
concentrationThe reaction mixture was concentrated under reduced pressure
filtrationfiltered by vacuum
concentrationThe filtrate was concentrated under reduced pressure
filtrationfiltered by vacuum filtration

Sources & evidence

ORD record: ord-7b5bbcc73bdf44b39dc24999d09baabe
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163008B2

Reaction notes

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