Sodium Hydroxide → Dimethyl-sulfamic Acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-yl ester

HRID 48460Notes

Reaction equation

HRID 48460 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:13]=[C:14]([OH:23])[C:15]3[CH:16]=[CH:17][N:18]([CH2:21][CH3:22])[C:19]=3[CH:20]=2)=[CH:6][N:5]=1.[CH3:24][N:25]([CH3:30])[S:26](Cl)(=[O:28])=[O:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[CH:17][N:18]3[CH2:21][CH3:22])=[C:14]([O:23][S:26](=[O:28])(=[O:27])[N:25]([CH3:30])[CH3:24])[CH:13]=2)=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 83372Dimethylsulphamoyl chloride2×HCID 227428966-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-ol

Product 1

HCID 69920737Dimethyl-sulfamic Acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-yl esterYield 9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrabutylammonium bromide (61 mg, 0.19 mmol) and 50% aqueous sodium hydroxide solution (7.8 mL) were added to a suspension of 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-ethyl-1H-indol-4-ol (Example 6; 436 mg, 1.54 mmol) in dichloromethane (130 mL), and the mixture was vigorously stirred for 15 min. Dimethylsulfamoyl chloride (226 mg, 1.57 mmol) was added, then after 2 h another portion of dimethylsulfamoyl chloride (60 mg, 0.42 mmol) was added. After 16 h the reaction mixture was partitioned between dichloromethane (130 mL) and water (50 mL), the organic layer was washed with brine, dried (MgSO4), and evaporated. The crude product was purified by preparative HPLC to afford the title compound (51 mg, 9%). Light brown solid.

Workup

  1. customAfter 16 h the reaction mixture was partitioned between dichloromethane (130 mL) and water (50 mL)
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ea18d9d8511a46418a9d7af36d3f7f0b
Source dataset
uspto-grants-2004_03
Patent number
US06703397B2

Reaction notes

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