Sodium hydride → HCID 21949395, compound

HRID 2376891Notes

Reaction equation

HRID 2376891 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.[CH2:20]([NH:22][C:23](=[O:31])OC1C=CC=CC=1)[CH3:21]>CN(C)C=O>[CH2:20]([NH:22][C:23]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([NH:10][C:6]3[CH:5]=[C:4]([NH:3][C:23]([NH:22][CH2:20][CH3:21])=[O:31])[N:9]=[CH:8][N:7]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:31])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2802346phenyl N-ethylcarbamateHCID 21949281HCID 21949281, compound

Product 1

HCID 21949395HCID 21949395, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (69 mg, 1.73 mmol) was suspended in N,N-dimethylformamide (3 ml); 6-amino-4-(1H-5-indolylamino)pyrimidine (311 mg, 1.38 mmol) was added thereto at room temperature under nitrogen stream; the reaction mixture was stirred for 30 minutes; phenyl N-ethylcarbamate (286 mg, 1.73 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; the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate; the solvent was distilled off; the residue was purified by silica gel column chromatography (eluent; ethyl acetate:tetrahydrofuran=1:1); 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 (14.3 mg, 0.039 mmol, 2.8%) 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. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:tetrahydrofuran=1:1)
  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-63a18645fc194056afc434706a6c2b29
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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