Hydrochloric Acid → 8-ethyl-4-methyl-2-[(4-piperazin-1-ylphenyl)amino]-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 886807Notes

Reaction equation

HRID 886807 reaction equation
Cl.[CH2:2]([N:4]1[C:9]2[N:10]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=[C:6]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)[C:5]1=[O:40])[CH3:3]>O1CCOCC1.CO>[CH2:2]([N:4]1[C:9]2[N:10]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=[C:6]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)[C:5]1=[O:40])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 57606982Tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate

Product 1

HCID 161243348-ethyl-4-methyl-2-[(4-piperazin-1-ylphenyl)amino]-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 74.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4M HCl in dioxane (3 mL) was added to a solution of tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate (99 mg, 0.181 mmol) in anhydrous methanol. After one h, a precipitate formed which was collected by vacuum filtration and identified as 8-ethyl-4-methyl-2-[(4-piperazin-1-ylphenyl)amino]-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (60 mg, 74% yield) as the HCl salt; MS calculated for C23H25N7OS.HCl: 447.5645, MS (EI) observed 448.1 (MH+).

Workup

  1. customAfter one h, a precipitate formed which
  2. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-906b61706f234499960d6cef9902e409
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

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