Triethylamine → N-([1,1′-Biphenyl]-4-ylmethyl)-2-chloro-9H-purin-6-amine

HRID 2215656Notes

Reaction equation

HRID 2215656 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[C:12]1([C:18]2[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(O)CCC>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:19][CH:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3449894-PhenylbenzylamineHCID 53244122,6-Dichloropurine

Product 1

HCID 21951838N-([1,1′-Biphenyl]-4-ylmethyl)-2-chloro-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

The 2,6-dichloropurine (5.0 g, 26.45 mmol) was suspended in n-butanol (50 ml) and the 4-phenylbenzylamine (6.61 g, 29.1 mmol) and triethylamine (4.1 ml, 29.1 mmol) were added. The solution was heated at 120° C. overnight then cooled. Filtered off product using excess n-butanol and washed precipitate with 100 ml 1M HCl and 200 ml water. The solid was dried in vacuum over overnight at 70° C. to give the desired product as a pale yellow solid

Workup

  1. temperaturethen cooled
  2. filtrationFiltered off product
  3. washwashed precipitate with 100 ml 1M HCl and 200 ml water
  4. customThe solid was dried in vacuum over overnight at 70° C.

Sources & evidence

ORD record
ord-d1da3c80250b492a81c5217cc28dacd6
Source dataset
uspto-grants-2006_09
Patent number
US07109330B2

Reaction notes

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