3-[2-(2-Ethylbenzoimidazol-1-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester → 3-[2-(2-Ethylbenzoimidazol-1-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethyl]azetidine-1-carboxylic acid tert-butyl ester

HRID 1945623Notes

Reaction equation

HRID 1945623 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[CH:12][C:13]2[S:21][C:20]3[C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:18][C:17]([N:28]4[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=[C:29]4[CH2:37][CH3:38])=[N:16][C:15]=3[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([CH2:12][C:13]2[S:21][C:20]3[C:19]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[N:18][C:17]([N:28]4[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=[C:29]4[CH2:37][CH3:38])=[N:16][C:15]=3[CH:14]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 596056083-[2-(2-Ethylbenzoimidazol-1-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596060703-[2-(2-Ethylbenzoimidazol-1-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethyl]azetidine-1-carboxylic acid tert-butyl esterYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-[2-(2-ethylbenzoimidazol-1-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester (1.5 g, 2.51 mmol) in EtOH (30 mL) was added 10% Pd/C (275 mg) and the resulting mixture stirred under an atmosphere of H2 for 65 h. The reaction mixture was filtered through Celite®, washing with EtOH, and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as an orange oil (0.71 g, 53%). LCMS (method A): RT 3.22 min [M+H]+ 535.4

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashing with EtOH
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)

Sources & evidence

ORD record
ord-c63fd325720b427a8d7819de214f1ffc
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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