6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one → HCID 5330293, compound

HRID 272471Notes

Reaction equation

HRID 272471 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21].[NH2:22][C:23]1[N:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([NH:22][C:23]3[N:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 113721276-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneHCID 223299261-(6-Aminopyridin-3-yl)piperidin-4-ol

Product 1

HCID 5330293HCID 5330293, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (2.50 g, 6.76 mmol) and 6′-amino-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-ol (1.96 g, 10.13 mmol) were combined in toluene (10.0 ml) under nitrogen. The reaction mixture was heated to reflux and stirred for 4 h. The reaction mixture was cooled to RT and filtered. The solids were washed with additional toluene (75 mL total) and dried in vacuo to produce a yellow powder (566 mg, 1.13 mmol). MS (APCI+) 499, 501 (M+2, 100); 1H NMR δ(400 MHz, DMSO-d6) 10.06 (s, 1H), 8.96 (s, 1H), 8.04 (s, 1H), 7.83 (d, J=9.3 Hz, 1H), 7.46 (d, J=7.3 Hz, 1H), 5.93-5.89 (m, 1H), 4.71 (s, 1H), 3.65-3.60 (m, 1H), 3.53-3.51 (m, 2H), 2.88-2.83 (m, 2H), 2.57 (s, 3H), 2.18 (br, 2H), 1.90-1.81 (m, 5H), 1.59-1.48 (m, 3H); Anal. Calc'd for C23H27Br1N6O2, 0.45H2O: C, 54.43; H, 5.54; N, 16.56. Found: C, 54.04; H, 5.23; N, 16.33.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe solids were washed with additional toluene (75 mL total)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7304a0ef5bce4d42a73f69311bab3388
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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