Sodium borohydride → 6-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-5-(2-thienylmethyl)-thieno[2,3-d]pyrimidine-2,4(1h,3h)-dione

HRID 379596Notes

Reaction equation

HRID 379596 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11](SC3SC=CC=3)=[C:12]([CH:14]=[O:15])[S:13][C:7]=2[N:6]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:5]1=[O:26]>CO.O>[OH:15][CH2:14][C:12]1[S:13][C:7]2[N:6]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:5](=[O:26])[N:4]([CH3:3])[C:9](=[O:10])[C:8]=2[C:11]=1[CH2:14][C:12]1[S:13][CH:7]=[CH:8][CH:11]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 183665901,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(thien-2-ylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 183665956-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-5-(2-thienylmethyl)-thieno[2,3-d]pyrimidine-2,4(1h,3h)-dioneYield 104.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (0.06 g) was added to 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(2-thienylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde (0.25 g) in methanol (25 ml) and the mixture was stirred for 24 hours. The reaction was diluted with water (30 ml) and was then extracted with ethyl acetate (3×50 ml). The organic phases were washed with brine and dried over magnesium sulfate, filtered and evaporated to leave a green oil. Purification by chromatography (1:4 ethyl acetate:isohexane) gave the subtitle compound as a yellow foam (0.125 g).

Workup

  1. extractionwas then extracted with ethyl acetate (3×50 ml)
  2. washThe organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto leave a green oil
  7. customPurification by chromatography (1:4 ethyl acetate:isohexane)

Sources & evidence

ORD record
ord-4345ed6075214854b0da1b7f053b2cf0
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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