Hydrochloric Acid → N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.5]decan-8-yl)pyrimidine-2,4-diamine

HRID 1477990Notes

Reaction equation

HRID 1477990 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=2)[N:21]=1)[CH:3]1[CH2:19][CH2:18][C:6]2([CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4]1.Cl>C(Cl)Cl.CCOC(C)=O>[CH3:1][N:2]([CH:3]1[CH2:19][CH2:18][C:6]2([CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4]1)[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=2)[N:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118390024tert-butyl 8-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate

Product 1

HCID 118410818N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.5]decan-8-yl)pyrimidine-2,4-diamineYield 70.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl 8-(methyl(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-2-azaspiro[4.5]decane-2-carboxylate (0.22 g, 0.50 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (10 mL, 3.5 M). The mixture was stirred at room temperature for 1.5 h, then concentrated in vacuo. The residue was diluted with DCM (10 mL) and saturated Na2CO3 (10 mL) and then extracted with DCM/MeOH (v/v)=10/1 (30 mL×4). The combined organic layers was dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/2M NH3 in MeOH (v/v)=5/1) to give the title compound as a yellow solid (0.12 g, 70%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with DCM (10 mL) and saturated Na2CO3 (10 mL)
  3. extractionextracted with DCM/MeOH (v/v)=10/1 (30 mL×4)
  4. dry with materialThe combined organic layers was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (DCM/2M NH3 in MeOH (v/v)=5/1)

Sources & evidence

ORD record
ord-51dbc434a1c74fa9b7b67bc039a0dd6d
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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