Methylamine → HCID 23356631, compound

HRID 233577Notes

Reaction equation

HRID 233577 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[N:5]2[N:20]=[CH:21][N:22]=[C:4]2[N:3]=1.CN.[CH2:25]([N:27](CC)CC)C>C1(C)C=CC=CC=1>[CH3:25][NH:27][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[N:5]2[N:20]=[CH:21][N:22]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 23356637HCID 23356637, compound

Product 1

HCID 23356631HCID 23356631, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-chloro-6-phenyl-7-cyclopentylamino-1,2,4-triazolo[1,5-a]pyrimidine (3.1 g, 10 mmol) prepared by a method analogous to Example 2, methylamine (5 ml), triethylamine (5 ml) and toluene (50 ml) was refluxed for 10 hours. After cooling, the reaction mixture was washed with water (50 ml) and the organic layer separated, dried over sodium sulphate and evaporated. Recrystallization of the solid residue from diisopropyl ether gave 2.3 g 5-methylamino-6-phenyl-7-cyclopentylamino-1,2,4-triazolo[1,5-a]pyrimidine as colourless crystals, m.pt. 158°-160° C. Yield: 75% of theoretical 1H-NMR: δ=1.25-1.7 (mm, 8H); 2.95 (d,3H); 3.42 (m,1H); 4.48 (m,1H); 5.55 (d,1H); 7.3-7.5 (m,5H); 8.03 (s,1H)

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water (50 ml)
  4. customthe organic layer separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customRecrystallization of the solid residue from diisopropyl ether

Sources & evidence

ORD record
ord-b91bce9732c44265a3abab0dd24cb6a0
Source dataset
uspto-grants-1997_01
Patent number
US05593996

Reaction notes

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