3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(6-chloro-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 2169641Notes

Reaction equation

HRID 2169641 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]([Cl:21])[CH:19]=4)[CH2:14][CH2:13]3)[C:7](=[O:22])[CH:6]3[CH2:23][O:24][CH2:25][CH2:26][N:5]3[C:4]=2[N:3]=1.[CH3:27][NH:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][CH:33]=1)=[O:30]>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]>[Cl:21][C:18]1[CH:19]=[C:20]2[C:15]([CH2:14][CH2:13][CH:12]2[N:8]2[C:7](=[O:22])[CH:6]3[CH2:23][O:24][CH2:25][CH2:26][N:5]3[C:4]3[N:3]=[C:2]([C:35]4[CH:34]=[CH:33][C:32]([NH:31][C:29]([NH:28][CH3:27])=[O:30])=[CH:37][CH:36]=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 866701162-chloro-5-(6-chloro-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 681954051-(4-(5-(6-chloro-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-chloro-2,3-dihydro-1H-inden-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x41, 90 mg, 0.230 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (127 mg, 0.460 mmol) and PdCl2(dppf) (8.42 mg, 0.012 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.36-2.45 (m, 2 H), 2.62-2.66 (d, 3 H), 3.08-3.22 (m, 3 H), 3.55-3.67 (m, 3 H), 3.95-4.10 (m, 1 H), 4.13-4.30 (m, 1 H), 4.38-4.66 (m, 2 H), 6.03-6.16 (m, 1 H), 7.14-7.43 (m, 4 H), 7.43-7.52 (d, 2 H), 8.03-8.16 (d, 2 H), 8.72-8.82 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C26H25ClN6O3, 505.17; found 505.4.

Sources & evidence

ORD record
ord-fbd6ff37d726408993af22298c2a08be
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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