Morpholine → 4-ethoxy-7-morpholino-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole

HRID 1182854Notes

Reaction equation

HRID 1182854 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([N:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[N:12]=[C:11]([O:21][CH2:22][CH3:23])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CC([O-])(C)C.[K+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:22]([O:21][C:11]1[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:3]=[CH:4][C:5]=3[C:6]=2[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:12]=1)[CH3:23]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23665647Potassium tert-butoxideHCID 66863934HCID 66863934, compound

Product 1

HCID 249905554-ethoxy-7-morpholino-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

100 mg (0.27 mmol) 7-bromo-4-ethoxy-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole (Example 4), 164 μl (1.86 mmol) morpholine, 179 mg (1.59 mmol) KOt-Bu, 1.2 mg (5.4 μmol) Pd(OAc)2 and 4.4 mg (21.6 μmol) P(t-Bu)3 were heated in 6 ml toluene in a microwave oven to 140° C. for 3 h. Then, the solvent was removed and the residue was purified by preparative HPLC (RP18). 8 mg (8%) of the title substance was obtained. ESI-MS [m/z]: 383 [M+H]+

Workup

  1. customThen, the solvent was removed
  2. customthe residue was purified by preparative HPLC (RP18)
  3. custom8 mg (8%) of the title substance was obtained

Sources & evidence

ORD record
ord-ed2c60174ba14b9b9f62dfc399ba6211
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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