4-[6-(8-Cyclopentyl-6-ethyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester → 8-cyclopentyl-6-ethyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

HRID 586452Notes

Reaction equation

HRID 586452 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]([CH2:31][CH3:32])[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.C(Cl)(Cl)[Cl:40].CO>>[ClH:40].[CH:34]1([N:27]2[C:25]3[N:26]=[C:21]([NH:20][C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][N:16]=4)[N:22]=[CH:23][C:24]=3[CH:30]=[C:29]([CH2:31][CH3:32])[C:28]2=[O:33])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 114097994-[6-(8-Cyclopentyl-6-ethyl-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 101516358-cyclopentyl-6-ethyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

Procedure

4-[6-(8-Cyclopentyl-6-ethyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.204 g, 0.39 mmol) prepared as in Example 4 was dissolved in 1:1 chloroform/methanol (16 ml) and purged with anhydrous hydrogen chloride gas. After stirring for 3.5 hours, addition of diethyl ether (8 ml) gave a solid precipitate. The solid was filtered, washed with diethyl ether and dried in vacuo yielding 0.180 g of 8-cyclopentyl-6-ethyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride as a yellow solid. MS (APCI); M++1: Calc'd, 420.52. Found, 420.2. Analyses for C34H29N7O.1.2H2O.2.1HCl. Calc'd: C, 53.36; H, 6.52; N, 18.93; Cl (ionic), 14.38; H2O, 4.17. Found: C, 53.25; H, 6.43; N, 18.80; Cl (ionic), 14.36; H2O, 3.87.

Workup

  1. custompurged with anhydrous hydrogen chloride gas
  2. additionaddition of diethyl ether (8 ml)
  3. customgave a solid precipitate
  4. filtrationThe solid was filtered
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9d5e051b7cdf4eb7af7a901514b27e2e
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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