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Potassium Carbonate → 8-bromo-7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

HRID 2200606
Notes
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Reaction equation

HRID 2200606 reaction equation
[Br:1][C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[NH:7][C:6](=[O:20])[N:5]([CH3:21])[C:4]=2[N:3]=1.Br[CH2:23][CH2:24][C:25]1([OH:28])[CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Br:1][C:2]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:23][CH2:24][C:25]3([OH:28])[CH2:27][CH2:26]3)[C:6](=[O:20])[N:5]([CH3:21])[C:4]=2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11089258-bromo-7-(4-chlorobenzyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione2×HCID 114237801-(2-Bromoethyl)cyclopropan-1-ol

Product 1

HCID 904028418-bromo-7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-1H-purine-2,6(3H,7H)-dioneYield 81.6%

Reagents, catalysts & solvents 2

HCID 67553
Tetrabutylammonium Iodide
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-bromo-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (150 mg, 0.405 mmol, intermediate 8) in DMF (5 mL) was added 1-(2-bromoethyl)cyclopropanol (94 mg, 0.568 mmol) followed by potassium carbonate (84 mg, 0.609 mmol) and TBAI (catalytic amount). The resulting mixture was stirred at 50° C. overnight. The reaction was diluted with ethyl acetated and washed with brine. The organic phase was dried and concentrated to give crude product which was purified via silica gel chromatography eluting with petroleum ether/ethyl acetate (5:1 to 2:1) to give 8-bromo-7-(4-chlorobenzyl)-1-(2-(1-hydroxycyclopropyl)ethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (150 mg, 81.6% yield) as light yellow solid. LCMS retention time 1.523 min; LCMS MH+ 455.

Workup

  1. additionThe reaction was diluted with ethyl
  2. washwashed with brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified via silica gel chromatography
  7. washeluting with petroleum ether/ethyl acetate (5:1 to 2:1)

Sources & evidence

ORD record
ord-a8fad07dc39f436fa4544d4028020f0b
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359359B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes