Sodium hydride → HCID 178462378, compound

HRID 60531Notes

Reaction equation

HRID 60531 reaction equation
[H-].[Na+].[BH4-].[Na+].O.[NH2:6][C:7]1[N:12]=[C:11]([SH:13])[N:10]=[C:9]([OH:14])[CH:8]=1.Cl[C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17]>CN(C=O)C>[NH2:6][C:7]1[N:12]=[C:11]([S:13][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[N:10]=[C:9]([OH:14])[CH:8]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 642190((1R)-1-Chloroethyl)benzeneHCID 4311764Sodium borohydrideHCID 178507962HCID 178507962, compound

Product 1

HCID 178462378HCID 178462378, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in oil) (0.5 g, 12.5 mmol) followed by NaBH4 (40 mg, 1 mmol) was added to 6-amino-2-mercaptopyrimidin-4-ol monohydrate (1.6 g, 10 mmol) in DMF (20 mL). After 30 min, [(1R)-1-chloroethyl]benzene (1.4 g, 10 mmol) was added and the reaction mixture was stirred for 16 h. The reaction was concentrated in vacuo to ca. 10 mL volume and then poured into water (ca. 50 mL). The precipitated solid material was filtered off and washed with water and ether to give the title compound (1.15 g, 46% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo to ca. 10 mL volume
  2. additionpoured into water (ca. 50 mL)
  3. filtrationThe precipitated solid material was filtered off
  4. washwashed with water and ether

Sources & evidence

ORD record
ord-fe4087e49a5f4d0798cd54d0f8e0d74f
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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