1H-Benzimidazol-4-ylboronic acid → 2-(1H-benzo[d]imidazol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169613Notes

Reaction equation

HRID 2169613 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.[NH:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24](B(O)O)[C:19]=2[N:18]=[CH:17]1>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]>[NH:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([C:2]3[N:11]=[CH:10][C:9]4[NH:8][CH2:7][CH:6]5[CH2:12][O:13][CH2:14][CH2:15][N:5]5[C:4]=4[N:3]=3)[C:19]=2[N:18]=[CH:17]1

Participants

6

Reactant 2

HCID 450778561H-Benzimidazol-4-ylboronic acidHCID 86670087HCID 86670087, compound

Product 1

HCID 601977672-(1H-benzo[d]imidazol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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 1 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 50 mg, 0.221 mmol), 1H-benzo[d]imidazol-4-ylboronic acid (71.5 mg, 0.441 mmol) and PdCl2(dppf) (12.91 mg, 0.018 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.03 (dd, J=11.87, 8.59 Hz, 1 H), 3.33-3.75 (m, 5 H), 3.98 (m, 2 H), 4.74-4.84 (m, 1 H), 6.49-7.07 (br s, 1 H), 7.54 (t, J=7.83 Hz, 1 H), 7.79-7.91 (m, 2 H), 8.25-8.33 (m, 1 H), 8.98 (s, 1 H), 12.18-12.29 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C16H16N6O, 309.14; found 309.3.

Sources & evidence

ORD record
ord-f08e3d28987a4ea5a9b8cd33a7ca60eb
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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