3-(Piperidinosulfonyl)aniline → 5-Methyl-N2-[3-(piperidine-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

HRID 1170732

Reaction equation

HRID 1170732 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([S:16]([C:19]2[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:16]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)(=[O:18])=[O:17])[CH:20]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 27947913-(Piperidinosulfonyl)anilineHCID 43021752-Chloro-5-methylpyrimidin-4-amine

Product 1

HCID 576750845-Methyl-N2-[3-(piperidine-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.25 g, 1.74 mmol) and 3-(piperidine-1-sulfonyl)-phenylamine (0.50 g, 2.1 mmol) in acetic acid (4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 130° C. for 15 min. After cooling to room temperature, the cap was removed and the mixture concentrated. The residue was taken in water (20 mL) and pH adjusted to ˜9 with 10% NaOH solution. The resulting solution was extracted with EtOAc (2×30 mL) and the organic layer separated. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the crude product (˜0.6 g) used in the next step without purification. MS (ES+): m/z 348 (M+H)+.

Workup

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 130° C. for 15 min
  3. customthe cap was removed
  4. concentrationthe mixture concentrated
  5. extractionThe resulting solution was extracted with EtOAc (2×30 mL)
  6. customthe organic layer separated
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe crude product (˜0.6 g) used in the next step without purification

Sources & evidence

ORD record
ord-f186316e4b4b41dd850c9e4b0e9dc188
Source dataset
uspto-grants-2010_11
Patent number
US07825246B2

Linked notes

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