Phenyl chloroformate → HCID 67219542, compound

HRID 916763Notes

Reaction equation

HRID 916763 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]2[C:12]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)=[O:14])=[CH:11][N:10]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:6]=2[N:7]=[CH:8][N:9]=1.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C1COCC1>[C:31]1([O:30][C:28](=[O:29])[NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:13]([C:12]3[C:5]4[C:4]([NH2:3])=[N:9][CH:8]=[N:7][C:6]=4[N:10]([CH:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)[CH:11]=3)=[O:14])[CH:16]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 24758Sodium hydrideHCID 11859044(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanone

Product 1

HCID 67219542HCID 67219542, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.21 g, 5.1 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (1.5 g, 4.7 mmol) in THF. (35 mL). After stirring for 1 h at room temperature, phenyl chloroformate (0.82 g, 5.4 mmol) was added. The resulting reaction mixture was stirred for an additional 3.5 h, quenched with water (15 mL), and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with saturated sodium bicarbonate (20 mL) and brine (20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude reaction mixture was triturated (CH2Cl2) and filtered to afford the title compound as a white solid (1.78 g, 87%). MS: 442.3 (MH+); HPLC Rf: 2.5 min. (HPLC method 2).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for an additional 3.5 h
  3. customquenched with water (15 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with saturated sodium bicarbonate (20 mL) and brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude reaction mixture
  10. customwas triturated (CH2Cl2)
  11. filtrationfiltered

Sources & evidence

ORD record
ord-5cfc22903b774f8b82f74d8169302214
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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