Tetrahydrofuran → HCID 55297730, compound

HRID 1094869Notes

Reaction equation

HRID 1094869 reaction equation
C1COCC1.[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([C:16](OCC)=[O:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOC(C)=O>[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 66641336Ethyl 4-aminopyrrolo[2,1-F][1,2,4]triazine-6-carboxylate

Product 1

HCID 55297730HCID 55297730, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of THF (150 mL) was added ethyl 4-aminopyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (2.29 g, 4.65 mmol) followed by 1 M DIBAL in THF (28.8 mL, 28.8 mmol). The solution was stirred at rt for 1 h. The r×n mixture was treated with EtOAc followed by aq Rochelle's salt. This heterogeneous mixture was then heated at 60° C. for 30 min. The solution was transferred to a separatory funnel, separated and washed with water. The aq layer was back extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated to yield 550 mg (93%) of the desired product. MS [M+H]+=165; LCMS RT=1.03.

Workup

  1. temperatureThis heterogeneous mixture was then heated at 60° C. for 30 min
  2. customThe solution was transferred to a separatory funnel
  3. customseparated
  4. washwashed with water
  5. extractionThe aq layer was back extracted with EtOAc
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5d91db0ec2ba4748a745fc258da7c999
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Reaction notes

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