Potassium Carbonate → 5-(4'-Dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine

HRID 963382

Reaction equation

HRID 963382 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16](I)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.[CH3:21][N:22]([CH3:33])[C:23]1[CH:28]=[CH:27][C:26](OB(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:21][N:22]([CH3:33])[C:23]1[CH:28]=[CH:27][C:26]([C:16]2[C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH2:6][C:7]3[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=3)[CH:15]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamineHCID 190817074-Dimethylamino-phenylboric acid

Product 1

HCID 190816835-(4'-Dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamineYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

376 mg of 5-(3,4-dimethoxy-5-iodo-benzyl)-pyrimidine-2,4-diamine and 400 mg of 4-dimethylamino-phenylboric acid (Example 3a)) are treated with 40 ml of dioxan and 2.4 ml of a 2M potassium carbonate solution and 24 mg of tetrakis-tri-phenylphosphine-palladium. The mixture is heated at reflux under argon for 14 hrs. Subsequently, it is poured on to ice-water, extracted with methylene chloride, dried over magnesium sulphate and chromatographed on silica gel with methylenechloride/methanol 98:2. 327 mg (91%) of 5-(4'-dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a yellowish solid. M.p. 230°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under argon for 14 hrs
  3. extractionextracted with methylene chloride
  4. dry with materialdried over magnesium sulphate
  5. customchromatographed on silica gel with methylenechloride/methanol 98:2

Sources & evidence

ORD record
ord-d1816e94275d4658bdec119882c1cb10
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Linked notes

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