Ammonia → 5-Chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-2,4-pyrimidinediamine

HRID 1777859Notes

Reaction equation

HRID 1777859 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[C:5]([Cl:21])=[CH:4][N:3]=1.[NH3:22]>CC(O)C>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[N:7][C:2]([NH2:22])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 597643782,5-dichloro-N-(2-((1-methylethyl)sulfonyl)phenyl)-4-pyrimidinamine

Product 1

HCID 707909185-Chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed tube, a mixture of 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (100 mg, 0.289 mmol) and ammonia (2 M in 2-propanol, 1.44 ml, 2.89 mmol) in 2-propanol (1.5 ml) was stirred at 80° C. for 2 days, then ammonia (2 M in 2-propanol, 1.44 ml, 2.89 mmol) was added and the reaction mixture was stirred at 80° C. for 7 days. The reaction mixture was cooled to room temperature and evaporated; the crude mixture was then diluted with EtOAc and washed with water; the organic phase was then dried over Na2SO4, filtered and evaporated to give the title compound as a yellow resin. (UPLC-MS 1) tR 0.83 min; ESI-MS 327.0 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 7 days
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customevaporated
  4. additionthe crude mixture was then diluted with EtOAc
  5. washwashed with water
  6. dry with materialthe organic phase was then dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-63c467ecb542441b9f9d4b915537ec7c
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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