Potassium Carbonate → HCID 59258991, compound

HRID 472207Notes

Reaction equation

Br[C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[CH3:21][O:22][CH2:23][O:24][CH2:25][CH2:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.C(=O)([O-])[O-].[K+].[K+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].CN(C=O)C>[CH:16]1([N:13]2[C:5]3[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=3[CH:3]=[C:2]([C:30]3[CH:29]=[N:28][N:27]([CH2:26][CH2:25][O:24][CH2:23][O:22][CH3:21])[CH:31]=3)[C:14]2=[O:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-bromo-8-cyclopentyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (200 mg, 0.56 mmol), 1-(2-(methoxymethoxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (239 mg, 1.5 equiv), palladium (0) tetrakis(triphenylphosphine) (6.13 mg, 0.05 equiv.), DMF (2 mL) in a 5 mL microwave vial was added potassium carbonate (3 M, 3.0 equiv). The solution was degassed with N2 for 10 min before being capped and heated in the microwave reactor for 30 min. at 100° C. The reaction was poured into 20 ml brine and the precipitate was collected by filtration. The title compound was obtained as a solid (208 mg, 86% yield). It was used for next step without further purification.

Workup

customThe solution was degassed with N2 for 10 min
custombefore being capped
additionThe reaction was poured into 20 ml brine
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-136911a5e9dc46afa9c468b71968787d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633204B2

Reaction notes

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