Nitrogen → US10023592, Example 225

HRID 575696Notes

Reaction equation

HRID 575696 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:21][CH2:22][CH2:23][CH3:24])=[C:10](B2OC(C)(C)C(C)(C)O2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2].Br[C:26]1[C:31]2[N:32]=[C:33]([C:36]3[CH:37]=[N:38][N:39]([CH3:41])[CH:40]=3)[N:34]=[CH:35][C:30]=2[C:29](=[O:42])[N:28]([CH3:43])[CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N#N>O1CCOCC1.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].C(Cl)Cl>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:21][CH2:22][CH2:23][CH3:24])=[C:10]([C:26]2[C:31]3[N:32]=[C:33]([C:36]4[CH:37]=[N:38][N:39]([CH3:41])[CH:40]=4)[N:34]=[CH:35][C:30]=3[C:29](=[O:42])[N:28]([CH3:43])[CH:27]=2)[CH:11]=1)(=[O:4])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 1180223108-Bromo-6-methyl-2-(1-methylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-oneHCID 1235700892-(5-Ethylsulfonyl-2-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118022134US10023592, Example 225Yield 83.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

The title compound of step 2 (60 mg, 0.17 mmol), the title compound of Example 224, step 4 (64 mg, 0.20 mmol), K3PO4 (108 mg, 0.51 mmol), and Pd(dppf)Cl2 (15 mg, 0.02 mmol) in dioxane (8 mL) were purged with N2 and heated at 70° C. for 18 h. CH2Cl2 extractive work up and preparative HPLC gave the title compound (66.11 mg, yield: 83.3%) as a grey solid. 1H NMR (CDCl3, 400 MHz) δ 9.64 (s, 1H), 8.19 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.06 (s, 1H), 7.96 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.70 (s, 1H), 7.15 (d, J=8.4 Hz, 1H), 4.03-3.95 (m, 5H), 3.67 (s, 3H), 3.20 (q, J=7.2 Hz, 2H), 1.67-1.60 (m, 2H), 1.36 (t, J=7.2 Hz, 3H), 0.81 (t, J=7.2 Hz, 3H). LCMS: 468.2 (M+1)+

Sources & evidence

ORD record
ord-2a823e2b511849f99572c7f471d7d08a
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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