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Cesium carbonate → HCID 57747299, compound

HRID 222075
Notes
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Reaction equation

HRID 222075 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 133964-AminobenzonitrileHCID 634876Binap, (A+-)-HCID 57747389HCID 57747389, compound

Product 1

HCID 57747299HCID 57747299, compound

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent

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

  1. customby bubbling nitrogen for 15 min
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes