5-Morpholinopyridin-2-amine → 8-cyclopentyl-6-ethoxymethyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 586546

Reaction equation

HRID 586546 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13](S(C)=O)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:19][O:20][CH2:21][CH3:22])[C:7]2=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:24]1([C:30]2[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:36][C:33]4[CH:32]=[CH:31][C:30]([N:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)=[CH:35][N:34]=4)[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:19][O:20][CH2:21][CH3:22])[C:7]2=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 113673465-Morpholinopyridin-2-amineHCID 117720128-cyclopentyl-6-ethoxymethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 102169938-cyclopentyl-6-ethoxymethyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneYield 17.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8-Cyclopentyl-6-ethoxymethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.60 g, 1.79 mmol) and 5-morpholin-4-yl-pyridin-2-ylamine (0.442 g, 2.47 mmol) were heated to reflux in toluene (6 mL) for 16 hours. The reaction mixture was cooled to room temperature and the precipitate that formed was filtered off and washed with toluene (2×4 mL) to give 8-cyclopentyl-6-ethoxymethyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (0.142 g, 17.6%). MS (APCI); M++1: Calc'd, 451.3. Found 451.3. Anal. Calc'd for C25H32N6O2: C, 63.98; H, 6.71; N, 18.65. Found: C, 64.03; H, 6.66; N, 18.49.

Workup

  1. customthe precipitate that formed
  2. filtrationwas filtered off
  3. washwashed with toluene (2×4 mL)

Sources & evidence

ORD record
ord-75936f88692f4e839701e7d36d8f7dc5
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Linked notes

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