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

HRID 324977Notes

Reaction equation

HRID 324977 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 (1) 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. For C15H16N5Cl(301.78) calculated: 59.70% C, 5.34% H, 23.21% N, 11.75% Cl; found: 59.52% C, 5.36% H, 23.01% N. FTIR spectrum (cm−1): 1713, 1626, 1572, 1537, 1497, 1471, 1456, 1425, 1398, 1355, 1314, 1292, 1255, 1228, 1202. ′H NMR (400 MHz, (CH3)2SO): 1.48D (6H, J=6.8, (CH3)2CH); 4.57 m (1H, CH(CH3)2); 4.66bd (2H, J=6.1, CH2); 7.19 ft, (1 H, J=7.2, J=1.7, H-p); 7.27dd (2H, J=7.2, H-m); 7.34dd (2H, J=7.2, J=1.7, H-o); 7.69s (1 H, H-C8).

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-9359cc4851904fa382db2ef256024ef8
Source dataset
uspto-grants-2001_04
Patent number
US06221873B1

Reaction notes

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