Water → HCID 118023102, compound

HRID 522645Notes

Reaction equation

HRID 522645 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)N=CN=1.C(C1C=NC([N:22]2[CH2:27][CH2:26][NH:25]CC2)=NC=1)C1C=CC=CC=1.CCN(C(C)C)[CH:31]([CH3:33])[CH3:32].[OH2:37].[O:38]1CCOC[CH2:39]1>>[CH3:32][C:31]1([CH3:33])[O:37][CH:2]([N:7]2[CH:6]=[C:26]([NH2:25])[CH:27]=[N:22]2)[CH2:39][O:38]1

Participants

6

Reactant 5

HCID 962WaterHCID 178102,4-Dichloro-1,3,5-triazineHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 53305546HCID 53305546, compound

Product 1

HCID 118023102HCID 118023102, compound

Procedure

A solution of 2,4-dichloro-1,3,5-triazine (315 mg, 2.1 mmol), 5-benzyl-2-(piperazin-1-yl)pyrimidine (510 mg, 2.0 mmol) and Hunig's base (540 mg, 4.2 mmol) in 1,4-dioxane (6 mL) was stirred at 60° C. for 1 h. LCMS showed the reaction was completed. The reaction mixture was cooled to RT, diluted by water (60 mL), and extracted with ethyl acetate (40 mL×3). The organic layers were combined, washed with water and brine, dried over sodium sulfate, filtered and concentrated to give 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-1H-pyrazol-4-amine (280 mg, crude) as a yellow solid, which was directly used in the next step without further purification. MS (ES+) C18H18ClN7 requires: 367, found: 368 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (40 mL×3)
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b6d46800a02441aa170f29965c7333c
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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