Cesium carbonate → HCID 70855692, compound

HRID 527866Notes

Reaction equation

HRID 527866 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10][C:11]1[NH:12][C:13]2[C:18]([N:19]=1)=[C:17]([NH2:20])[N:16]=[CH:15][N:14]=2.Br[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:20][C:17]1[N:16]=[CH:15][N:14]=[C:13]2[C:18]=1[N:19]=[C:11]([S:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[I:1])[N:12]2[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10513201HCID 10513201, compoundHCID 178491880HCID 178491880, compound

Product 1

HCID 70855692HCID 70855692, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-((2-iodo-5-methoxyphenyl)thio)-9H-purin-6-amine (200 mg, 0.5 mmol) in DMF (3 mL) was added N-(3-bromopropyl)pivalamide (445 mg, 2 mmol) and Cs2CO3 (326 mg, 1 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS64 as a white solid (53 mg, 20%). 1H NMR (500 MHz, CDCl3): δ 8.26 (s, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.43 (br s, 1H), 6.66 (s, 1H), 6.50 (d, J=8.7 Hz, 1H), 5.86 (br s, 2H), 4.20 (t, J=6.1 Hz, 2H), 3.61 (s, 3H), 2.78 (m, 2H), 1.82 (m, 2H), 1.21 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 178.8, 160.5, 155.0, 153.2, 152.0, 145.0, 140.6, 137.7, 120.1, 117.2, 115.4, 88.4, 55.5, 40.7, 38.8, 34.8, 29.1, 27.7; HRMS (ESI) m/z [M+H]+ calcd. for C20H26IN6O2S, 541.0883. found 541.0898.

Workup

  1. customcondensed under vacuum
  2. customthe residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1)

Sources & evidence

ORD record
ord-dd477ff606724e74b684c2dee77e9f68
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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