Ammonia → HCID 19081745, compound

HRID 963378Notes

Reaction equation

HRID 963378 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH2:5][C:6]1[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[N:10][CH:11]=1.[Cl-].[Li+].C([C:27]1[C:32](O)=[C:31](C(C)(C)C)[CH:30]=[C:29](C)[CH:28]=1)(C)(C)C.N>O1CCOCC1>[CH3:20][O:19][C:15]1[CH:14]=[C:4]([CH2:5][C:6]2[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[N:10][CH:11]=2)[CH:3]=[C:2]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 30080143-Desmethoxy-3-bromo Trimethoprim

Product 1

HCID 19081745HCID 19081745, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

138 mg of 5-(3-bromo-4,5-dimethoxy-benzyl)-pyrimidine-2,4-diamine, 98 mg of trimethyl-phenyl-stannate (Example 1a), 51 mg of lithium chloride, 25 mg of tetrakis-triphenylphosphinepalladium and a crystal of 2,6-di-t-butyl-p-cresol in 10 ml of dioxan are held at reflux under argon for 4 hrs. The yellowish reaction mixture is poured into about 10% aqueous ammonia and extracted three times with methylene chloride. The organic phase is dried over magnesium sulphate and chromatographed on silica gel with methylene chloride/methanol 9:1. 62 mg (46%) of 5-(5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a yellowish solid. Mass spectrum: peaks: inter alia at m/e: 336 (M+, 100%), 321 (28%), 305 (54%), 123 (36%).

Workup

  1. temperatureat reflux under argon for 4 hrs
  2. customThe yellowish reaction mixture
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customchromatographed on silica gel with methylene chloride/methanol 9:1

Sources & evidence

ORD record
ord-7a172e9aa1e6452286b28987818e38e6
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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