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2-(Tributylstannyl)-1,3-thiazole → 2-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 886805
Notes
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Reaction equation

HRID 886805 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:16])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([CH2:14][CH3:15])[C:6]=2[N:7]=1.C([Sn](CCCC)(CCCC)[C:22]1[S:23][CH:24]=[CH:25][N:26]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([CH3:16])[C:5]2[CH:11]=[C:10]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)[C:9](=[O:13])[N:8]([CH2:14][CH3:15])[C:6]=2[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 576069632-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 161233812-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140
Toluene
Solvent

Conditions

Temperature
110 °C

Procedure

To a pressure tube charged with 2-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (500 mg, 1.77 mmol) and 2-tributylstannylthiazole (793 mg, 3.54 mmol) in dry toluene (6.0 mL) was added Pd(PPh3)4 (204 mg, 0.177 mmol). The pressure tube was sealed under nitrogen and heated to 110° C. After 12 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was redissolved in ethyl acetate and 40% KF on alumina (2 g) added. After 30 minutes, the alumina was filtered and the filtrate washed consecutively with 1M aqueous KF and brine. The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with methylene chloride and hexanes to provide 2-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (178 mg, 35% yield) as a yellow solid. MS calculated for C13H13N5OS 287.346, MS (EI) observed 288.0 (MH+).

Workup

  1. customThe pressure tube was sealed under nitrogen
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was redissolved in ethyl acetate
  5. addition40% KF on alumina (2 g) added
  6. waitAfter 30 minutes
  7. filtrationthe alumina was filtered
  8. washthe filtrate washed consecutively with 1M aqueous KF and brine
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was triturated with methylene chloride and hexanes

Sources & evidence

ORD record
ord-19d52697b8574047975f4dd44dc472eb
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247408B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes