Potassium Carbonate → HCID 59279645, compound

HRID 2047662Notes

Reaction equation

HRID 2047662 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1>CN(C=O)C>[CH:27]1([CH2:26][N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([F:1])=[N:3][C:4]=3[NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 12111407HCID 12111407, compound

Product 1

HCID 59279645HCID 59279645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-fluoro-6-[(pyridin-3-ylmethyl)-amino]purine (1 g, 4.10 mmol) in DMF (12 ml) under argon atmosphere, at RT, was added K2CO3 (powdered, anhydrous, 2.84 g, 5 eq, 20.52 mmol) followed by (bromomethyl)cyclopropane (5.53 g 10 eq, 41 mmol). The reaction mixture was stirred at RT for 24 h, when TLC (CHC13: Me0H; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between water (50 ml) and EtOAc (50 mL); the aqueous phase was separated and extracted with more EtOAc (2×50 ml). The bulked organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient flash column chormoatography on silica gel, eluted with CHCl3:MeOH (100:0→95:5), to afford the product as a colorless gum; Yield 0.8 g (68%) δH (250 MHz, CDCl3) 0.24-0.15 (2 H, m, CHH and CHH of Cp), 0.48-0.38 (2 H, m, CHH and CHH of Cp), 1.11-0.95 (1 H, m, CH of Cp), 2.56 (1 H, s, br, NH), 3.69 (2 H, d, J 7.5, HCH2Cp), 4.58 (2 H, s, br, HCH2Ar), 7.04-6.96 (1 H, m, ArH), 7.51-7.45 (2 H, m, ArH), 8.26-8.24 (1 H, m, ArH), 8.37 (1 H, s, br, ArH); δc (250 MHz, CDCl3) 156.32 (C), 156.01 (C), 149.29 (CH), 148.97 (CH), 139.85 (CH), 139.8 (C), 135.54 (CH), 133.81 ©, 123.51 (CH, 117.86 (C), 48.52 (CH2), 42.09 (CH2), 11.06 (CH3), 5.28 (2×(CH2); m/z 299.2 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between water (50 ml) and EtOAc (50 mL)
  3. customthe aqueous phase was separated
  4. extractionextracted with more EtOAc (2×50 ml)
  5. washThe bulked organic phase was washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customthe residue was purified by gradient flash column chormoatography on silica gel
  9. washeluted with CHCl3:MeOH (100:0→95:5)

Sources & evidence

ORD record
ord-36e933861c794ebaadbf89a78fefb116
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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