Sodium hydride → HCID 10277546, compound

HRID 1295475Notes

Reaction equation

HRID 1295475 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[SH:12].Br[C:14]1[N:15]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:16]2[C:21]([N:22]=1)=[C:20]([NH2:23])[N:19]=[CH:18][N:17]=2>CN(C=O)C>[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[S:12][C:14]1[N:15]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:16]2[C:21]([N:22]=1)=[C:20]([NH2:23])[N:19]=[CH:18][N:17]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11551089HCID 11551089, compoundHCID 58893098HCID 58893098, compound

Product 1

HCID 10277546HCID 10277546, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (96 mg, 4 mmol) in DMF (3 ml) was added 2-iodo-5-methoxy-benzenethiol (1.06 g, 4 mmol; J Org. Chem, 2001, 66(13), 4525-4542). After 30 min, a solution of 8-bromo-9-(4-methyl-pent-3-enyl)-9H-purin-6-ylamine (296 mg, 1 mmol) in DMF (3 ml) was added, and the mixture was stirred for 12 h at 70° C. The reaction was quenched by addition of MeOH (2 ml), diluted with EtOAc (200 ml), washed with Na2CO3 (3×50 ml), brine (3×50 ml), dried (Na2SO4), evaporated, and purified by flash chromatography (CH2Cl2: MeOH=100:5) to give 8-(2-Iodo-5-methoxy-phenylsulfanyl)-9-(4-methyl-pent-3-enyl)-9H-purin-6-ylamine as a colorless powder (280 mg, 58%).

Workup

  1. customThe reaction was quenched by addition of MeOH (2 ml)
  2. additiondiluted with EtOAc (200 ml)
  3. washwashed with Na2CO3 (3×50 ml), brine (3×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. custompurified by flash chromatography (CH2Cl2: MeOH=100:5)

Sources & evidence

ORD record
ord-347c73bfc1ed41c29026cca7d0b62947
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Reaction notes

Loading…