2-Bromopropane → N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine

HRID 48182Notes

Reaction equation

HRID 48182 reaction equation
[CH2:1]([NH:8][C:9]1[N:17]=[C:16]([Cl:18])[N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:25](Br)([CH3:27])[CH3:26]>CS(C)=O>[CH2:1]([NH:8][C:9]1[N:17]=[C:16]([Cl:18])[N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 10777711N-Benzyl-2-chloro-9H-purin-6-amine

Product 1

HCID 10733091N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amineYield 85.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6-benzylamino-2-chloropurine (Hocart C. H., Letham D. S., Parker C. W.: Phytochemistry 30,2477 (1991)) 1.32 g, 5.08 mmol), potassium carbonate (4.3 g, 31 mmol) and isopropylbromide (5.5 ml, 58 mmol) in 35 ml of dry dimethyl sulfoxide was vigorously shaken overnight. The reaction mixture was evaporated in vacuum and then partitioned between water and ethylacetate. The organic layer was dried (sodium sulfate) and evaporated. Crystallization from methanol afforded 1.305 g (85%) of product 2, m.p. 181-182° C.

Workup

  1. customThe reaction mixture was evaporated in vacuum
  2. custompartitioned between water and ethylacetate
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customevaporated
  5. customCrystallization from methanol

Sources & evidence

ORD record
ord-3bb061161c654ea3a1dc05a8a01128d2
Source dataset
uspto-grants-2004_03
Patent number
US06703395B2

Reaction notes

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