Cesium carbonate → Methyl (+)-{4-[4-(4-Amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]cyclohex-3-en-1-yl}acetate

HRID 2237633Notes

Reaction equation

HRID 2237633 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([C:13]3[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1.[CH3:21][O:22][C:23](=[O:40])[CH2:24][CH:25]1[CH2:30][CH2:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH2:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C:28]4[CH2:29][CH2:30][CH:25]([CH2:24][C:23]([O:22][CH3:21])=[O:40])[CH2:26][CH:27]=4)=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 59302514Methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]acetateHCID 593025304-Amino-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one

Product 1

HCID 59302505Methyl (+)-{4-[4-(4-Amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]cyclohex-3-en-1-yl}acetate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 4-amino-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one (40 mg, 0.10 mmol), methyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]acetate (38 mg, 0.14 mmol), cesium carbonate (42 mg, 0.28 mmol) and palladium tetrakis(triphenyl-phosphine) (6 mg, 0.005 mmol) in 1,2-dimethoxyethane (1.0 mL) was heated at 100° C. for 18 hours. The reaction mixture was cooled, concentrated and chromatographed to afford a white solid, 19 mg. IC50 84.3 nM.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customchromatographed
  4. customto afford a white solid, 19 mg

Sources & evidence

ORD record
ord-61e114b4f87a4dfe8c0065beba5699c2
Source dataset
uspto-grants-2010_05
Patent number
US07718645B2

Reaction notes

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