Sodium Carbonate → 5-(2,6-Diethoxy-3'-methylsulphanyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

HRID 2416302Notes

Reaction equation

HRID 2416302 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].[CH3:23][S:24]([C:27]1[CH:28]=[C:29]([B])[CH:30]=[CH:31][CH:32]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][C:8]2[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1[C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([S:24][CH3:23])[CH:32]=1)[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 226369195-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamineHCID 867595603-Methylsulphonyl-phenylboron

Product 1

HCID 226369295-(2,6-Diethoxy-3'-methylsulphanyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamineYield 63%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Starting from 5-(3,5-diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (178 mg; 0.43 mmol), 3-methylsulphonyl-phenylboron acid (140 mg; 0.86 mmol) and tetrakis-triphenylphosphine-palladium (69 mg; 0.060 mmol) in dimethoxyethane (4 ml), ethanol (3 ml) and sodium carbonate (387 mg; 3.6 mmol) in water (4.5 ml), 10 mg (63%) 5-(2,6-diethoxy-3′-methylsulphanyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine are obtained as a greyish powder analogously to example 2a after crystallization from methanol.

Sources & evidence

ORD record
ord-508b9a554b7d41e6973cbf0255022d3a
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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