HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Adenine → 9-(Phenylmethyl)-9H-purin-6-amine

HRID 1297150
Notes
Print preview

Reaction equation

HRID 1297150 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 190AdenineHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 202629-(Phenylmethyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of adenine (5) (5.00 g, 37.0 mmol) in dry DMF (120 mL) was added NaH (1.77 g, 44.4 mmol) at room temperature. The reaction mixture was stirred for 30 min and the resulting white suspension was warmed to 60° C. for an additional 30 min. Benzyl bromide (7.59 g, 44.4 mmol) was added and the mixture was stirred for 24 h at 60° C. TLC of the reaction mixture indicated the formation of two products. DMF was distilled off under reduced pressure and the resulting residue was treated with water (20 mL). The white solid that separated out, was filtered and dried under vacuum. Separation and purification was through flash column chromatography using CHCl3::MeOH (9:1) for elution. 9-Benzyladenine: yield 5.5 g. (66%); mp 231-232° C.; 1H NMR (DMSO-d6,: δ 5.38 (s, 2H, CH2), 7.29-7.33 (m, 7H, Ar—H and NH2), 8.17 (s, 1H, purine C8—H), 8.28 (s, 1H, purine C2—H). 7-Benzyladenine: yield 1.8 g. (21%). Mp 252-255° C. 1H NMR (DMSO-d6): δ 5.53 (s, 2H, CH2), 7.29-7.48 (m, 5H, Ar—H), 7.81 (s, 1H, purine C8—H), 8.0-8.1 (br, 2H, NH2), 8.6 (s, 1H, purine C2—H).

Workup

  1. stirringthe mixture was stirred for 24 h at 60° C
  2. distillationDMF was distilled off under reduced pressure
  3. additionthe resulting residue was treated with water (20 mL)
  4. customThe white solid that separated out
  5. filtrationwas filtered
  6. customdried under vacuum
  7. customSeparation and purification
  8. washMeOH (9:1) for elution

Sources & evidence

ORD record
ord-876262c0be254120ba2da76ee0d52dbc
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07250421B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes