Sodium borohydride → 5-[(3-Hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-[1-hydroxy-1-(pyridin-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379587Notes

Reaction equation

HRID 379587 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]=2[S:8][C:7]=1[C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23].[BH4-].[Na+]>C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]=2[S:8][C:7]=1[CH:22]([OH:23])[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 98029245-[(3-Hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-[(pyridin-3-yl)carbonyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 183665885-[(3-Hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-[1-hydroxy-1-(pyridin-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[(3-hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-[(pyridin-3-yl)carbonyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.35 g, Example 37) in dry ethanol (40 ml) at 0° C. was added sodium borohydride (0.03 g). The reaction was allowed to warm to room temperature and stirred for 2 hours. The solution was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal-phase HPLC eluting with a gradient of 0-5% ethanol in dichloromethane to give the title compound as a white foam. (0.27 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by normal-phase HPLC
  7. washeluting with a gradient of 0-5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-a0fa25b0e8f14c8d8d948686f71ae4dc
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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