Borohydride → HCID 13304947, compound

HRID 371394Notes

Reaction equation

HRID 371394 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 (0.525 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 (6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)methanol (93% yield as a white crystalline solid melting 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-cc3e8e602ebb4b37b96629719084e6df
Source dataset
uspto-grants-1985_07
Patent number
US04532243

Reaction notes

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