Diethyl Ether → 6-bromo-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

HRID 1271921Notes

Reaction equation

HRID 1271921 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[CH:30]=[C:29]([Br:31])[C:28](=[O:32])[N:27]([CH:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)C.C(Cl)(Cl)[Cl:44].CO>>[ClH:44].[Br:31][C:29]1[C:28](=[O:32])[N:27]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]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[CH:30]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 113765404-[6-(6-Bromo-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl esterHCID 21584188Chloroform methanol

Product 1

HCID 101960146-bromo-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

Procedure

4-[6-(6-Bromo-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.26 g, 0.46 mmol) prepared as in Example 2 was dissolved in 1:1 chloroform/methanol (15 ml), to which was added diethyl ether (25 ml). The solution was purged with anhydrous hydrogen chloride gas and stoppered for 18 hours. The resulting white solid was filtered, washed with diethyl ether and dried in vacuo at 60° C. to give 6-bromo-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride as a pale yellow solid (0.254 g). MS (APCI); M++1: Calc, 470.12, Found, 470.0. Analyses for C21H24BrN2O.1.25 H2O.2.2HCl: Calc'd: C, 44.01; H, 5.05; N, 17.11, Cl (ionic), 13.61; H2O, 3.93. Found: C, 43.74; H, 5.07; N, 16.78; Cl (ionic), 13.73 ; H2O, 3.81

Workup

  1. customThe solution was purged with anhydrous hydrogen chloride gas
  2. filtrationThe resulting white solid was filtered
  3. washwashed with diethyl ether
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-e1f152612f1b417ab1393b9575c9cc64
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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