2-Bromopropane → HCID 57433116, compound

HRID 2047661Notes

Reaction equation

HRID 2047661 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]1[N:15]=[C:14]([F:16])[N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][NH:11]2.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:29])[CH3:28].C(Cl)Cl.CCOCC.CO>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]1[N:15]=[C:14]([F:16])[N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][N:11]2[CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 22565053DCM ether MeOHHCID 178505711HCID 178505711, compound

Product 1

HCID 57433116HCID 57433116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (3-fluoro-benzyl)-(2-fluoro-9H-purin-6-yl)-amine (0.6 g, 2.24 mmol) in dimethylformamide (10 ml) at room temperature under an argon atmosphere, was added powdered, anhydrous potassium carbonate (1.52 g, 5 eq, 11.2 mmol), followed by 2-bromopropane (2.3 ml, 10 eq, 22.4 mmol). The reaction mixture was stirred at room temperature for 24 h, when DCM:ether:MeOH (55:40:5), indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous phase was extracted with more ethyl acetate (2×50 ml) and the combined organic phase washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash silica gel column chromatography, eluted with chloroform to afford the title compound as a slightly yellow gum; Yield: 0.37 g (54%). δH (250 MHz, CDCl3) 1.55 (6 H, d, J 7.5, CH[CH3]2), 4.85-4.65 (3 H, m, NHCH2Ar and CHMe2), 5.96 (1 H, s, br, NH), 7.31-6.94 (4 H, m, ArH), 7.59 (1 H, s, br, ArH); δC (250 MHz, CDCl3) 164.93 (C), 161.01 (C), 156.04 (C), 139.77 (C), 137.76 (CH), 130.13 (CH), 129.92 (C), 123.19 (CH), 114.59 (CH), 114.26 (CH), 47.22 (CH), 43.93 (CH2), 22.56 (2×CH3); m/z 304.2 (M+H)

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. extractionThe aqueous phase was extracted with more ethyl acetate (2×50 ml)
  4. washthe combined organic phase washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash silica gel column chromatography
  8. washeluted with chloroform

Sources & evidence

ORD record
ord-412708dc11dc41b8b5488a218d111c73
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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