Triethylamine → HCID 21473626, compound

HRID 2294045Notes

Reaction equation

HRID 2294045 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br.Br.Br[CH2:24][C:25]1[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:24][C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 21473626HCID 21473626, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.6 g (0.020 mol) of 4-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridine in 100 ml of tetrahydrofuran was treated with 13.9 ml (0.10 mol) of triethylamine and 7.3 g (0.020 mol) of 5-bromomethyl-pyrimidine-2,4-diamine dihydrobromide and the mixture was stirred at room temperature under argon for 16 hours. The suspension obtained was suction filtered and the filtrate was completely freed from the solvents. The residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether. 3.5 g (58%) of 5-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-pyrimidine-2,4-diamine were obtained as brownish crystals; m.p. 265°.

Workup

  1. customThe suspension obtained
  2. filtrationfiltered
  3. customThe residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether

Sources & evidence

ORD record
ord-5034413593d14ae6aaea98455f32980e
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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