Purine → HCID 11254459, compound

HRID 348393Notes

Reaction equation

HRID 348393 reaction equation
N1C=C2C(N=CN2)=NC=1.[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([NH:15][CH:16]=[N:17]2)=[C:13]([Cl:20])[N:12]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(N(CC)CC)C>ClCCl>[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C:25]2[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=2)=[C:13]([Cl:20])[N:12]=1

Participants

6

Reactant 4

HCID 1044PurineHCID 8471TriethylamineHCID 79799Tolylboronic acidHCID 53244122,6-Dichloropurine

Product 1

HCID 11254459HCID 11254459, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Purine N9 arylation via boronic acids/cupric acetate: A 20 mL glass vial equipped with a magnetic stir bar was charged with 2,6-dichloropurine (0.200 g, 1.06 mmol, 1.0 equiv), 4-methylphenylboronic acid (0.288 g, 2.12 mmol, 2.0 equiv), anhydrous cupric acetate (0.384 g, 2.12 mmol, 2.0 equiv.), 4 Å activated molecular sieves (0.500 g), triethylamine (0.443 mL, 3.18 mmol, 3.0 equiv.) and dichloromethane (5.0 mL). The reaction was stirred under air at ambient temperature and monitored by TLC. When the reaction was complete after 24 hours, it was filtered through Celite, washed with methanol and purified by flash column chromatography (1% methanol in dichloromethane) to afford desired 2,6-dichloro-9-(4-methylphenyl)-purine (0.136 g, 47%). 1H NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 7.41 (d, 2H, J=8.1 Hz), 7.54 (d, 2H, J=8.1 Hz), 8.35 (s, 1H); HRMS (MALDI-FTMS) C12H8Cl2N4 [MH+] 279.0199, found: 279.0208.

Workup

  1. filtrationit was filtered through Celite
  2. washwashed with methanol
  3. custompurified by flash column chromatography (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4c7b3876e35844dc9a2fb45a9481a828
Source dataset
uspto-grants-2007_02
Patent number
US07176312B2

Reaction notes

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