3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6-oxo-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

HRID 2169642Notes

Reaction equation

HRID 2169642 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[CH2:14][CH2:13]3)[C:7](=[O:23])[CH:6]3[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]=2[N:3]=1.[CH3:28][NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=1)=[O:31]>O1CCOCC1.C([O-])(O)=O.[Na+].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]>[CH3:22][O:21][C:18]1[CH:19]=[C:20]2[C:15]([CH2:14][CH2:13][CH:12]2[N:8]2[C:7](=[O:23])[CH:6]3[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]3[N:3]=[C:2]([C:36]4[CH:35]=[CH:34][C:33]([NH:32][C:30]([NH:29][CH3:28])=[O:31])=[CH:38][CH:37]=4)[N:11]=[CH:10][C:9]2=3)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 177502733-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 866701182-chloro-5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 681946081-(4-(5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6-oxo-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-5-(6-methoxy-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x43, 70 mg, 0.181 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (100 mg, 0.362 mmol) and PdCl2(dppf) (6.62 mg, 9.05 μmol) in dioxane (3 mL) and aqueous saturated NaHCO3 (0.6 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.23-2.45 (m, 3 H), 2.60-2.66 (m, 3 H), 2.87-3.17 (m, 4 H), 3.55-3.72 (m, 4 H), 3.95-4.10 (m, 1 H), 4.16-4.34 (m, 1 H), 4.38-4.64 (m, 2 H), 6.04-6.15 (m, 1 H), 6.49-6.91 (m, 3 H), 7.23-7.34 (m, 1 H), 7.41-7.50 (m, 2 H), 8.04-8.14 (m, 2 H), 8.72-8.81 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C27H28N6O4, 501.22; found 501.5.

Sources & evidence

ORD record
ord-eff24ea23d634bdc9ae9b83443349426
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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