Sodium hydride → HCID 58792217, compound

HRID 2376892Notes

Reaction equation

HRID 2376892 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:5]=1.[CH3:20][CH:21]([NH:23][C:24](=[O:32])OC1C=CC=CC=1)[CH3:22]>CN(C)C=O>[CH3:20][CH:21]([NH:23][C:24]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([NH:10][C:6]3[CH:5]=[C:4]([NH:3][C:24]([NH:23][CH:21]([CH3:20])[CH3:22])=[O:32])[N:9]=[CH:8][N:7]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:32])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 302841phenyl N-isopropylcarbamateHCID 21949281HCID 21949281, compound

Product 1

HCID 58792217HCID 58792217, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (48 mg, 1.2 mmol) was suspended in N,N-dimethylformamide (2.5 ml); 6-amino-4-(1H-5-indolylamino)pyrimidine (225.3 mg, 1.0 mmol) was added thereto at room temperature under nitrogen stream; the reaction mixture was stirred for 30 minutes; phenyl N-(2-propyl)carbamate (215 mg, 1.2 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1) and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent; ethyl acetate); eluted fractions were concentrated; ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (31.3 mg, 0.079 mmol, 7.9%) as white crystals.

Workup

  1. customat room temperature
  2. stirringand the reaction mixture was stirred overnight
  3. customThe reaction mixture was partitioned between a solvent mixture of ethyl acetate-tetrahydrofuran (1:1)
  4. washand the organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)
  8. concentrationeluted fractions were concentrated
  9. additionethyl acetate was added to the residue
  10. customto crystallize
  11. filtrationand the crystals were filtered off
  12. customdried under aeration

Sources & evidence

ORD record
ord-27f29297a1274387b9ad079acf6c4478
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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