Sodium Carbonate → HCID 24938134, compound

HRID 2365189Notes

Reaction equation

HRID 2365189 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH3:25][C:26]1[CH:27]=[CH:28][C:29](B2OC(C)(C)C(C)(C)O2)=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([C:2]2[N:3]=[C:4]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=2)=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 574203384-(2-Chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholineHCID 67361721HCID 67361721, compound

Product 1

HCID 24938134HCID 24938134, compoundYield 70.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 2-Chloro-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (0.23 mmol, 84 mg) and 7-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (0.46 mmol, 117 mg) in toluene (2 mL), ethanol (1 mL) and water (0.5 mL) was added sodium carbonate (0.69 mmol, 73 mg). Pd (PPh3)2Cl2 (0.012 mmol, 8 mg) was added and the mixture heated in a microwave reactor at 130° C. for 1.5 hours. The mixture was allowed to cool and partitioned between water and dichloromethane. The combined organic layers were washed with brine, separated and dried (MgSO4). The solvent was evaporated and the crude product purified by column chromatography to yield 2-(7-methyl-1H-indol-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a pale cream solid (75 mg).

Workup

  1. temperatureto cool
  2. custompartitioned between water and dichloromethane
  3. washThe combined organic layers were washed with brine
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe crude product purified by column chromatography

Sources & evidence

ORD record
ord-cb4cbd53dc044347a262e2a77facf663
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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