Hydrochloric Acid → 6-Bromo-8-cyclopentyl-5-methyl-2-(5-piperizin-1-yl-pyridin-2-ylamino)-8H-pyrido(2,3-d)pyrimidin-7-one Hydrochloride

HRID 586461Notes

Reaction equation

HRID 586461 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:30]([CH3:31])=[C:29]([Br:32])[C:28](=[O:33])[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.Cl>C(Cl)Cl.CCOCC>[Br:32][C:29]1[C:28](=[O:33])[N:27]([CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:25]2[N:26]=[C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:15][N:16]=3)[N:22]=[CH:23][C:24]=2[C:30]=1[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11157536tert-Butyl 4-(6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido(2,3-d)pyrimidin-2-ylamino)-pyridin-3-yl)-piperazine-1-carboxylate

Product 1

HCID 53302846-Bromo-8-cyclopentyl-5-methyl-2-(5-piperizin-1-yl-pyridin-2-ylamino)-8H-pyrido(2,3-d)pyrimidin-7-one Hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.04 g, 0.07 mmol) was suspended in CH2Cl2 (10 mL) and MeOH was added in order to produce a solution (up to 6 mL). 2 M HCl in ether (10 mL) was added with stirring. The reaction mixture was stirred at room temperature for a total of 3 days then the solvents were removed by evaporation at reduced pressure. The remaining solid was suspended in ether and filtered to give 6-bromo-8-cyclopentyl-5-methyl-2-(5-piperizin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid, which was dried in vacuo at 50° C. MS (APCI); M++1: Calc'd, 486.15. Found, 486.1. Analyses for C23H26N7OBr.2.64H2O.2.0HCl: Calc'd: C, 43.68; H, 5.55; N, 16.21; Cl (ionic), 11.72. Found: C, 44.08; H, 5.32; N, 15.23; Cl (ionic), 11.65.

Workup

  1. customto produce a solution (up to 6 mL)
  2. stirringThe reaction mixture was stirred at room temperature for a total of 3 days
  3. customthe solvents were removed by evaporation at reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d19517c0f7e34cdbbc00611dd07794fa
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

Loading…