Borohydride → HCID 13304947, compound

HRID 280087Notes

Reaction equation

HRID 280087 reaction equation
[BH4-].[Li+].[CH2:3]([C:5]1[C:6]([O:20][CH3:21])=[N:7][C:8]2[N:9]([CH:12]=[C:13]([C:15](OCC)=[O:16])[N:14]=2)[C:10]=1[CH3:11])[CH3:4].[BH4-]>O1CCCC1>[CH2:3]([C:5]1[C:6]([O:20][CH3:21])=[N:7][C:8]2[N:9]([CH:12]=[C:13]([CH2:15][OH:16])[N:14]=2)[C:10]=1[CH3:11])[CH3:4]

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 4148881Lithium borohydrideHCID 13304946HCID 13304946, compound

Product 1

HCID 13304947HCID 13304947, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.55 g (0.0525 mol) of lithium borohydride were added portionwise over 1 hour to a stirred solution of 19.7 g (75 mmol) of ethyl 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxylate in 300 ml of dry tetrahydrofuran and after stirring at room temperature for 18 hours the excess borohydride was destroyed by dropwise addition of 300 ml of saturated sodium chloride solution. Then, the mixture was stirred for 30 minutes before separating the organic layer. The aqueous layer was extracted with chloroform and the combined extracts were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to obtain 15.4 g of (6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)methanol (93% yield) as a white crystalline solid metling at 186°-188° C. (decomp.).

Workup

  1. customwas destroyed by dropwise addition of 300 ml of saturated sodium chloride solution
  2. custombefore separating the organic layer
  3. extractionThe aqueous layer was extracted with chloroform
  4. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-40b77288454f4e658d358f2fabc57fa8
Source dataset
uspto-grants-1986_05
Patent number
US04588720

Reaction notes

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