Sodium Bicarbonate → HCID 59592817, compound

HRID 2098709Notes

Reaction equation

HRID 2098709 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[C:20]=2[CH:19]=[CH:18]1.C(=O)([O-])O.[Na+]>COCCOC.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:17]1[C:25]2[C:20](=[C:21]([C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[N:7]=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine

Product 1

HCID 59592817HCID 59592817, compoundYield 25.3%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-4-morpholin-4-yl-thieno-[3.2-d]pyrimidine 4 (120 mg), 4-indole-boronic acid (110 mg), sodium hydrogen carbonate (120 mg) and PdCl2(PPh3)2 (30 mg) in DME (3 ml) and water (1 ml) were heated in a microwave for 90 min at 130° C. Dichloromethane/water extraction and purification on silica gave 199 (40 mg). NMR: (400 MHz, CDCl3): 3.95 (4H, t, J=4.5), 4.13 (4H, t, J=4.5), 7.30-7.38 (2H, m), 7.52 (1H, d, J=8.1), 7.55-7.59 (2H, m), 7.75 (1H, d, J=5.5), 8.22 (1H, d, J=7.4), 8.30 (1H, br) MS: (ESI+): MH+ 337

Workup

  1. extractionDichloromethane/water extraction and purification on silica

Sources & evidence

ORD record
ord-4f4c0c1354364c9db4ebf9a3f9e148f1
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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