Hydrazine hydrate (1:1) → HCID 59173582, compound

HRID 220088Notes

Reaction equation

HRID 220088 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O.[NH2:18][NH2:19]>CC(O)C>[C:1]([O:5][C:6](=[O:16])[N:7]([C:9]1[CH:14]=[C:13]([NH:18][NH2:19])[N:12]=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59173508HCID 59173508, compound

Product 1

HCID 59173582HCID 59173582, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (6-Chloro-pyrimidin-4-yl)-methyl-carbamic acid tert-butyl ester (10 g, 41.1 mmol), hydrazine monohydrate (6.5 g, 130.0 mmol), and 2-propanol (50 mL) is heated to 90° C. for 4 hours. The reaction mixture is then cooled to room temperature, and concentrated. The resultant crude product is treated with a mixture of water (80 mL) and ethanol (15 mL), heated for 30 minutes, and slowly cooled to room temperature. White precipitate forms. After filtration, the undissolved solid is washed with water, dried under vacuum overnight to give (6-Hydrazino-pyrimidin-4-yl)-methyl-carbamic acid tert-butyl ester as white powder in needle form: 1H NMR 400 MHz (d6-DMSO) δ 8.23 (s, 1H), 8.19 (s, 1H), 7.14 (s, 1H), 4.29 (s, 2H), 3.23 (s, 3H), 1.49 (s, 9H); MS m/z 240.10 (M+1).

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. concentrationconcentrated
  3. additionThe resultant crude product is treated with a mixture of water (80 mL) and ethanol (15 mL)
  4. temperatureheated for 30 minutes
  5. temperatureslowly cooled to room temperature
  6. filtrationAfter filtration
  7. washthe undissolved solid is washed with water
  8. customdried under vacuum overnight

Sources & evidence

ORD record
ord-66c25089e062477ba345d002508e5b3c
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

Loading…