2-Aminopyridine → HCID 5330261, compound

HRID 586448Notes

Reaction equation

HRID 586448 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]=[CH:8][C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[N:14]=[CH:15][C:10]=3[CH:9]=[CH:8][C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 108263958-Cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 5330261HCID 5330261, compoundYield 7%

Conditions

Temperature
160 °C

Procedure

8-Cyclopentyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (200 mg, 0.7 mmol) prepared as in Example 107 of WO 98/33798 (incorporated herein by reference) and 2-aminopyridine (130 mg, 1.4 mmol) were combined in a 10 mL round-bottomed flask. The flask was purged with nitrogen (10 min), then heated in a 160° C. oil bath (30 min). After cooling, the orange residue was triturated with water to afford an orange solid, which was further purified by reversed-phase HPLC purification. [Vydac C18 TP254 (30 mm×100 mm); A: ACN (acetonitrile)+0.1% TFA (trifluor acetic acid); B; H2O+0.1% TFA; 10%-76% B over 40 min]. 15 mg of 8-cyclopentyl-2-(pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one was isolated as a yellow solid. Mp: >250° C., Anal. HPLC [Vydac C18 TP254 (4.6×150 mm); A: ACN+0.1% TFA; B; H2O+0.1% TFA; 10%-76% B over 20 min]: >98% Rt=13.9 min.

Workup

  1. customwere combined in a 10 mL round-bottomed flask
  2. customThe flask was purged with nitrogen (10 min)
  3. temperatureAfter cooling
  4. customthe orange residue was triturated with water
  5. customto afford an orange solid, which
  6. customwas further purified by reversed-phase HPLC purification

Sources & evidence

ORD record
ord-8aab31c2d30f41dd871a33670afe2d84
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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