Hydrazine hydrate (1:1) → 5-(2-aminoethyl)-6-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrimidin-4-amine

HRID 1747671Notes

Reaction equation

HRID 1747671 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)=[C:6]([NH:21][C@@H:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23]2)[N:5]=[CH:4][N:3]=1.O.NN>C(O)C>[NH2:10][CH2:9][CH2:8][C:7]1[C:6]([NH:21][C@@H:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23]2)=[N:5][CH:4]=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596713922-(2-{4-chloro-6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-5-yl}ethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 596712355-(2-aminoethyl)-6-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrimidin-4-amineYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-{4-chloro-6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-5-yl}ethyl)-1H-isoindole-1,3(2H)-dione (3.50 g, 8.32 mmol) was suspended in ethanol (102 mL) and hydrazine hydrate (1.62 mL, 33.3 mmol) was added. The mixture was heated to reflux for 1 hour. At that time, LCMS indicated complete conversion. The mixture was cooled to 23 OC, crystals were filtered off, the residue was evaporated in vacuo and purified using chromatography on silica gel using gradient 0 to 20% MeOH in methylene chloride to afford the title compound (1.20 g, 50%). LC/MS: Rt=1.29 min, ES+ 289 (AA standard).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was cooled to 23 OC, crystals
  4. filtrationwere filtered off
  5. customthe residue was evaporated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-e67ae8131e324a69881a3e9798db8997
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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