Hydrochloric Acid → HCID 86673118, compound

HRID 1853357Notes

Reaction equation

HRID 1853357 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[N:20]=[CH:19][N:18]3[CH:21]=[CH:22][CH:23]=[C:17]3[CH:16]=1)=[CH:9][C:8]2=[N:24][O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O.CC(C[AlH]CC(C)C)C.Cl>ClCCl.C1COCC1>[C:26]([O:25][N:24]=[C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([CH2:3][OH:2])[CH:6]=2)[O:11][C:10]([C:15]2[N:20]=[CH:19][N:18]3[CH:21]=[CH:22][CH:23]=[C:17]3[CH:16]=2)=[CH:9]1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydride2×HCID 86673092HCID 86673092, compound

Product 1

HCID 86673118HCID 86673118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(tert-Butoxyimino)-2-pyrrolo[1,2-c]pyrimidin-3-yl-4H-chromene-6-carboxylic acid methyl ester (example 115B) (574 mg, 1.46 mmol) in dichloromethane (9 ml) at 0° C. was added a 1M solution of DIBAL-H in THF (12.8 ml). After 2 hours at 0° C. an additional amount of 1M solution of DIBAL-H in THF (6 ml) was added to complete the reaction. After hydrolysis with a 1M aqueous solution of hydrogen chloride, the reaction mixture was extracted with ethyl acetate. The organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated. The product was used without further purification.

Workup

  1. customthe reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-66a4dbb208f94a82b6a1661e05607647
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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