Barium hydroxide → HCID 86723424, compound

HRID 2201309Notes

Reaction equation

[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)=[C:6]2[C:5](=[O:31])[N:4]([CH3:32])[C:3]1=[O:33])[CH2:12][CH2:11][CH:10]=[C:9]3B1OC(C)(C)C(C)(C)O1.I[C:35]1[S:36][CH:37]=[C:38]([CH3:40])[N:39]=1.[OH-].[Ba+2].[OH-]>C(#N)C.O.Cl>[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)=[C:6]2[C:5](=[O:31])[N:4]([CH3:32])[C:3]1=[O:33])[CH2:12][CH2:11][CH:10]=[C:9]3[C:35]1[S:36][CH:37]=[C:38]([CH3:40])[N:39]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,3-dimethyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-m-tolyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (step 5) (295 mg, 0.66 mmol), 2-iodo-4-methylthiazole (Intermediate O) (135 mg, 0.60 mmol), Pd-118 (19.6 mg, 0.03 mmol) and barium hydroxide (206 mg, 1.20 mmol) in acetonitrile/water (1:1, 3 mL) was stirred at 80° C. for 30 minutes. The reaction mixture was diluted with 1M HCl (5 mL) and extracted with DCM (3×5 mL). The combined organic layers were filtered through a hydrophobic frit and the solvent was removed under vacuum. The residue was purified by chromatography on silica, eluting with 1-2% MeOH/DCM to give the title compound.

Workup

extractionextracted with DCM (3×5 mL)
filtrationThe combined organic layers were filtered through a hydrophobic frit
customthe solvent was removed under vacuum
customThe residue was purified by chromatography on silica
washeluting with 1-2% MeOH/DCM

Sources & evidence

ORD record: ord-9006d3d590e840cc90551d77f33b8d6a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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