Sodium Bicarbonate → HCID 86618406, compound

HRID 2098696Notes

Reaction equation

HRID 2098696 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=[O:12])=[CH:8][C:6]=2[N:7]=1.[NH:19]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[C:22]=2[CH:21]=[CH:20]1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:19]1[C:27]2[C:22](=[C:23]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([CH:11]=[O:12])=[CH:8][C:6]=4[N:7]=3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86618406HCID 86618406, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 (200 mg), 4-indole-boronic acid (125 mg), sodium hydrogen carbonate (178 mg) and PdCl2(PPh3)2 (4 mg) in toluene (1.5 ml), ethanol (0.75 ml) and water (0.4 ml) were heated in a microwave at 120° C. for 45 min. Chloroform/water extraction and purification on silica gave 2-(1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (257 mg).

Workup

  1. extractionChloroform/water extraction and purification on silica

Sources & evidence

ORD record
ord-cc294f43eef0421e8731cfe8aac13a93
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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