Potassium Carbonate → HCID 178515104, compound

HRID 497130Notes

Reaction equation

HRID 497130 reaction equation
Cl[CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:11](=[O:20])[C:10]2[C:5](=[CH:6][C:7]([N+:21]([O-:23])=[O:22])=[CH:8][CH:9]=2)[N:4]=1.O.[SH:25][C:26]1[N:34]=[CH:33][N:32]=[C:31]2[C:27]=1[NH:28][CH:29]=[N:30]2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[C:11](=[O:20])[C:10]2[C:5](=[CH:6][C:7]([N+:21]([O-:23])=[O:22])=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:2][S:25][C:26]1[N:34]=[CH:33][N:32]=[C:31]2[C:27]=1[N:28]=[CH:29][NH:30]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22316553HCID 22316553, compoundHCID 178527204HCID 178527204, compound

Product 1

HCID 178515104HCID 178515104, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure C using Intermediate 2o (216 mg, 0.617 mmol), 6-mercaptopurine monohydrate (116 mg, 0.681 mmol), K2CO3 (94 mg, 0.680 mmol), and DMF (4 mL). The crude product was recrystallized from EtOH to provide 212 mg of a yellow crystalline solid (74%), mp 218.0-218.3° C. (decomposes). 1H NMR (DMSO-d6) δ: 13.56 (br s, 1H); 8.49 (s, 1H); 8.42 (s, 1H); 8.38-8.45 (m, 2H); 8.31 (d, J=8.4 Hz, 1H); 7.81 (d, J=6.5 Hz, 1H); 7.68 (d, J=6.7 Hz, 1H); 7.43-7.58 (m, 2H); 4.53 (s, 2H). 13C NMR (DMSO-d6) ppm: 157.7, 154.4, 153.3, 149.8, 149.3, 147.6, 145.2, 141.4, 131.5, 129.8, 129.7, 129.2, 128.4, 127.1, 126.7, 122.7, 120.3, 119.4, 29.9. MS (ES): m/z 466.0 (M+). Anal. calcd. for C20H12ClN7O3S.0.4C2H6O.0.05KCl: C, 51.19; H, 2.97; Cl, 7.63; N, 20.09; S, 6.57. Found: C, 51.27; H, 2.88; Cl, 7.40; N, 20.04; S, 6.52.

Workup

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

Sources & evidence

ORD record
ord-ab37f0163ac840168ff3a18bef10cad3
Source dataset
uspto-grants-2005_09
Patent number
US06949535B2

Reaction notes

Loading…