Cesium carbonate → HCID 57747299, compound

HRID 222075Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:7]=[N:8]2)=[C:4]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[N:3]=1.[NH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[C:5]3[C:9](=[N:10][C:2]([NH:33][C:34]4[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=4)=[N:3][C:4]=3[O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)[N:8]=[CH:7]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-chloro-7-(4-methoxybenzyl)-6-(4-(pyridin-4-yl)phenoxy)-7H-purine (48 mg, 0.11 mmol), 4-aminobenzonitrile (20 mg, 0.17 mmol), Pd(OAc)2(2 mg, 0.009 mmol), BINAP (9 mg, 0.014 mmol), and Cs2CO3 (43 mg, 0.13 mmol) in toluene (2 mL) was degassed by bubbling nitrogen for 15 min then heated at 80° C. overnight. The desired product was precipitated with EtOAc (10 mL) and saturated NaHCO3. NMR (DMSO-d6): 10.00 (s, 1H), 8.70 (d, 2H), 8.41 (s, 1H), 7.98 (d, 2H), 7.82 (d, 2H), 7.75 (d, 2H), 7.53 (m, 4H), 7.38 (d, 2H), 6.98 (d, 2H), 5.38 (s, 2H), 3.74 (s, 3H); MS (ESI): m/z 526 (M+1)+.

Workup

customby bubbling nitrogen for 15 min
customThe desired product was precipitated with EtOAc (10 mL) and saturated NaHCO3

Sources & evidence

ORD record: ord-bacb557050944828b6e6d6686f36517e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207178B2

Reaction notes

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