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

HRID 1007157Notes

Reaction equation

HRID 1007157 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-amineYield 99%

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 vaccum over overnight at 70° C. to give the desired product as a pale yellow solid. Yield=99%.

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 vaccum over overnight at 70° C.

Sources & evidence

ORD record
ord-affb7cac8a014839a912d297c39378f3
Source dataset
uspto-grants-2004_09
Patent number
US06794390B2

Reaction notes

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