Ammonia → 5-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

HRID 79111

Reaction equation

HRID 79111 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH3:16].C(OCC)(=O)C>C(O)(C)C>[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 595508905-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

Product 1

HCID 582996735-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamineYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of compound 32 (6.60 g, 23 mmol) in isopropyl alcohol (40 ml) was added ammonia (aq. 28%, 80 ml). This reaction mixture was heated to 130° C. for 14 hours in a pressure vessel. The reaction mixture was cooled down to room temperature and to this mixture was added ethyl acetate. The reaction mixture was washed with water and brine. The ethyl acetate layer was dried with sodium sulfate and concentrated to give compound 33 (4.75 g, 77%). 1H NMR (500 MHz, CD3OD) δ ppm 7.79 (1 H, s), 4.24 (1 H, m), 3.99-4.02 (2 H, dd, J=11.0, 2.2 Hz), 3.52 (2 H, td, J=11.9, 2.0 Hz), 1.92-1.96 (2 H, m), 1.69 (2 H, m); LCMS-ESI (POS), M/Z, M+1: Found 273, Calculated 273.0

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature and to this mixture
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialThe ethyl acetate layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6229f9a396354562be7e42eb4230bbe6
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Linked notes

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