Potassium Phosphate, Tribasic → US10023592, Example 224

HRID 575694Notes

Reaction equation

HRID 575694 reaction equation
Br[C:2]1[C:7]2[N:8]=[C:9]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[N:10]=[CH:11][C:6]=2[C:5](=[O:18])[N:4]([CH3:19])[CH:3]=1.[CH:20]1([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:26]=2B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:20]1([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:26]=2[C:2]2[C:7]3[N:8]=[C:9]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)[N:10]=[CH:11][C:6]=3[C:5](=[O:18])[N:4]([CH3:19])[CH:3]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1180223108-Bromo-6-methyl-2-(1-methylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-oneHCID 1234348592-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118022011US10023592, Example 224Yield 35.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound of step 4 (200 mg, 0.627 mmol), the title compound of Example 90, step 1 (266 mg, 0.752 mmol), K3PO4 (400 mg, 1.881 mmol) and Pd(dppf)Cl2 (10 mg) in dioxane (4 mL) and H2O (1 mL) were heated at 70° C. for 18 h under N2. After preparative HPLC, the title compound (104.5 mg, 35.8%) was obtained as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 9.64 (s, 1H), 8.24-8.18 (m, 2H), 8.07 (s, 1H), 7.96 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.77 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 3.95 (s, 3H), 3.91 (d, J=7.2 Hz, 2H), 3.68 (s, 3H), 3.12 (s, 3H), 1.13-1.01 (m, 1H), 0.54-0.44 (m, 2H), 0.21-0.14 (m, 1H). LCMS: 466.1 (M+1)+

Sources & evidence

ORD record
ord-0335c39985c94c07b8097f8bd1b1175b
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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