Triethylamine → HCID 24849198, compound

HRID 2246472Notes

Reaction equation

HRID 2246472 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[C:16](=[O:29])[N:17]([CH3:28])[C:18]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:19][CH:20]=3)=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33]C.ClC(OC1C=CC=CC=1)=[O:39].N1CCCC1>C1COCC1>[CH3:28][N:17]1[C:16](=[O:29])[C:15]([C:12]2[N:13]=[CH:14][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:33]([N:32]4[CH2:35][CH2:36][CH2:30][CH2:31]4)=[O:39])[CH:7]=3)=[CH:10][CH:11]=2)=[CH:20][N:19]=[C:18]1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 25000866HCID 25000866, compound

Product 1

HCID 24849198HCID 24849198, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(5-(2-aminopyridin-4-yloxy)pyridin-2-yl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (128.6 mg, 0.333 mmol) was dissolved in THF (5.0 ml) and Et3N (0.10 ml, 0.72 mmol) and phenyl chloroformate (0.070 ml, 0.56 mmol) were added via syringe, and the reaction was stirred at room temperature. After about 45 minutes, pyrrolidine (0.31 ml, 3.7 mmol) was added, and the reaction was stirred at room temperature overnight. The next morning, the reaction was quenched with saturated ammonium chloride (5 ml) and extracted with DCM (3×15 ml). The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel column (30:1->20:1 DCM/2 N ammonia in MeOH). The fractions with product collected, concentrated, washed with Et2O, and filtered. The solid collected was washed with Et2O and acetone and filtered again. The solid was collected and dried under vacuum to give the desired titled compound N-(4-(6-(1-methyl-6-oxo-2-(phenylamino)-1,6-dihydropyrimidin-5-yl)pyridin-3-yloxy)pyridin-2-yl)pyrrolidine-1-carboxamide (17.4 mg, 0.0360 mmol, 11% yield). MS (ESI pos. ion) m/z: 484 (MH+). Calc'd exact mass for C26H25N7O3: 483.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe next morning, the reaction was quenched with saturated ammonium chloride (5 ml)
  3. extractionextracted with DCM (3×15 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a silica gel column (30:1->20:1 DCM/2 N ammonia in MeOH)
  8. customThe fractions with product collected
  9. concentrationconcentrated
  10. washwashed with Et2O
  11. filtrationfiltered
  12. customThe solid collected
  13. washwas washed with Et2O and acetone
  14. filtrationfiltered again
  15. customThe solid was collected
  16. customdried under vacuum

Sources & evidence

ORD record
ord-e66aa886545343db8b13958c4f926095
Source dataset
uspto-grants-2010_03
Patent number
US07687522B2

Reaction notes

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