Sodium hydride → HCID 178479939, compound

HRID 2424374Notes

Reaction equation

HRID 2424374 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[H-].[Na+].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1.[NH4+:24].[Cl-]>CN(C=O)C>[NH2:24][C:20]1([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]3)[C:19]([Cl:23])=[CH:18][N:17]=[C:16]([Cl:15])[NH:21]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2372592,4,5-TrichloropyrimidineHCID 450887127-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 178479939HCID 178479939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At 0° C., a solution of 7-Amino-N-methyl-2,3-dihydroisoindole-1-one (232.6 mg, 1.43 mmol) in DMF (2.0 mL) is treated with 60% NaH (89.8 mg), stirred at the same temperature for 1.5 h, treated with a solution of 2,4,5-trichloropyrimidine (0.557 g) in DMF (3.5 mL), stirred for 1 h, and warmed to room temperature. After furthermore stirring for 13 h, the mixture is treated with sat. aqueous NH4Cl (6 mL), and the resulting brown precipitates are collected by a filtration, followed by washing with H2O, hexane, and CH3CN to give 7-(4-Amino-2,5-dichloropyrimidin-4-yl)amino-N-methyl-2,3-dihydroisoindole-1-one (130.2 g, 0.416 mmol) in 26%. Brown solid. Rf (CH2Cl2/EtOAc 1:1) 0.50. 1H-NMR (400 MHz, CDCl3): 3.22 (s), 4.43 (s), 7.15 (d, J=8.0), 7.59 (dd, J=8.0, 8.0), 8.24 (s), 8.71 (d, J=8.0), 11.05 (br. s).

Workup

  1. stirringstirred for 1 h
  2. stirringAfter furthermore stirring for 13 h
  3. customthe resulting brown precipitates
  4. filtrationare collected by a filtration
  5. washby washing with H2O, hexane, and CH3CN

Sources & evidence

ORD record
ord-d846021ee468453c85c31d81e336ec92
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

Loading…