Sodium Carbonate → HCID 57898018, compound

HRID 1693531Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[S:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([C:33]3[CH:34]=[CH:35][S:31][CH:32]=3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A solution of 1-(4-chloro-phenyl)-2-(4-iodo-phenyl)-9-phenyl-1,9-dihydro-purin-6-one (20 mg, 0.038 mmol), 3-thiophene boronic acid (9.7 mg, 0.076 mmol) and tetrakis(triphenylphosphine) palladium (4.4 mg, 0.0038 mmol) in 1 mL of toluene is added 2.0 M Na2CO3 solution (200 μL). The reaction mixture is heated at 170° C. on the microwave oven for 20 min. After cooled down, the resulting solution is concentrated and purified with HPLC. 1H NMR (CDCl3) δ(ppm) 8.12 (s, 1H), 7.71 (d, 2H), 7.57 (t, 2H), 7.47 (m, 4H), 7.38 (m, 1H), 7.33 (m, 5H), 7.14 (d, 2H); HPLC-MS calculated for C27H17ClN4OS (M+H+): 481.0. Found 481.0.

Workup

temperatureAfter cooled down
concentrationthe resulting solution is concentrated
custompurified with HPLC

Sources & evidence

ORD record: ord-b93b84dff1a54f55bdad6b507104cf22
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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