Adenine → 2-(6-Aminopurin-9-ylmethyl)-3-biphenyl-2-yl-5-chloro-3H-quinazolin-4-one

HRID 497118Notes

Reaction equation

HRID 497118 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Cl:18])[N:9]=[C:8]1[CH2:19]Cl.[N:27]1[C:35]([NH2:36])=[C:34]2[C:30]([N:31]=[CH:32][NH:33]2)=[N:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:36][C:35]1[N:27]=[CH:28][N:29]=[C:30]2[C:34]=1[N:33]=[CH:32][N:31]2[CH2:19][C:8]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Cl:18])[N:9]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 11430Potassium CarbonateHCID 223165793-Biphenyl-2-yl-5-chloro-2-chloromethyl-3H-quinazolin-4-one

Product 1

HCID 101166652-(6-Aminopurin-9-ylmethyl)-3-biphenyl-2-yl-5-chloro-3H-quinazolin-4-oneYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure C using Intermediate 2i (400 mg, 1.05 mmol), adenine (155 mg, 1.15 mmol), K2CO3 (159 mg, 1.15 mmol), and DMF (5 mL). The crude product was recrystallized from EtOH to provide 344 mg of a white solid (68%), mp 299.9-300.1° C. (discolors). 1H NMR (DMSO-d6) δ: 8.08 (s, 1H); 7.89 (s, 1H); 7.58-7.73 (m, 5H); 7.51 (d, J=7.9 Hz, 1H); 7.46 (d, J=7.5 Hz, 2H); 7.27-7.41 (m, 3H); 7.14-7.27 (m, 3H); 5.14 (d, J=17 Hz, 1H); 4.82 (d, J=17 Hz, 1H). 13C NMR (DMSO-d6) ppm: 159.6, 156.2, 152.8, 152.5, 150.0, 149.0, 141.7, 140.2, 137.7, 135.0, 133.3, 133.2, 131.8, 130.7, 130.1, 129.8, 129.5, 128.8, 128.6, 128.4, 127.1, 118.4, 117.6, 45.3. MS (ES): m/z 480.1 (M+). Anal. calcd. for C26H18ClN7O: C, 65.07; H, 3.78; Cl, 7.39; N, 20.43. Found: C, 64.77; H, 3.75; Cl, 7.43; N, 20.35.

Workup

  1. customPrepared
  2. customThe crude product was recrystallized from EtOH

Sources & evidence

ORD record
ord-045f4eaf2e7d4d979a10208fe8bc9a2d
Source dataset
uspto-grants-2005_09
Patent number
US06949535B2

Reaction notes

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