Sodium hydride → HCID 59924748, compound

HRID 2300796Notes

Reaction equation

HRID 2300796 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[H-].[Na+].[C:14]1([C@@H:20]([NH:22][C:23]2[N:28]=[C:27](Cl)[CH:26]=[CH:25][N:24]=2)[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[C:14]1([C@@H:20]([NH:22][C:23]2[N:24]=[C:25]([N:8]3[C:4]4[CH:3]=[C:2]([NH2:1])[C:10]([CH3:11])=[CH:9][C:5]=4[N:6]=[CH:7]3)[CH:26]=[CH:27][N:28]=2)[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59924636HCID 59924636, compoundHCID 178422329HCID 178422329, compound

Product 1

HCID 59924748HCID 59924748, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-amino-6-methybenzimidazole (28 mg, 0.19 mmol, 1 eq) in DMF was added NaH (60% dispersion in oil, 7.6 mg, 0.19 mmol, 1 eq). After gas evolution ceased, 2-[(S)-1-phenylethylamino]-4-chloro-pyrimidine (45 mg, 0.19 mmol, 1 eq) was added and the mixture was warmed to 90° C. and stirred 7 h. The heating bath was turned off and the mixture was allowed to stir overnight at room temperature. The DMF was removed under reduced pressure. The residue was diluted with water and extracted wth CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The products were purified by preparative thin layer chromatography to afford 10.5 mg of 2-[(S)-1-phenylethylamino]-4-[5-methyl-6-amino-benzimidazol-1-yl]pyrimidine 1H NMR (500 MHz, CDCl3): δ 1.64 (3H, d, J=7 Hz), 2.27 (3H, s), 3.59 (2H, br s), 5.23 (1H, br m), 5.75 (1H, br s), 6.71 (1H, d, J=5.5 Hz), 7.04 (1H, br), 7.31 (1H, t, J=7.5 Hz), 7.40 (2H, t, J=7.5 Hz), 7.47 (2H, d, J=7.5 Hz), 8.25 (1H, br s), 8.35 (1H, d, J=5.5 Hz). Mass spectrum (ESI) 345.2 (M+1). and 10.3 mg of 2-[(S)-1-phenylethylamino]-4-[5-amino-6-methyl-benzimidazol-1-yl]pyrimidine 1H NMR (500 MHz, CDCl3): δ 1.65 (3H, d, J=7 Hz), 2.31 (3H, s), 3.68 (2H, br s), 5.26 (1H, m), 5.74 (1H, br s), 6.75 (1H, d, J=5.5 Hz), 7.11 (1H, s), 7.28 (1H, m), 7.37 (2H, t, J=7 Hz), 7.75 (2H, d, J=7 Hz), 7.75 (1H, br s), 8.34 (1H, d, J=5.5 Hz), 8.38 (1H, br s). Mass spectrum (ESI) 345.2 (M+1).

Workup

  1. stirringto stir overnight at room temperature
  2. customThe DMF was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted wth CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe products were purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-0a7b89e51eb444bdab9c400525c7fbe5
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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