Sodium hydride → HCID 178462379, compound

HRID 550765Notes

Reaction equation

HRID 550765 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][C:19]=1[F:24])[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][C:19]=2[F:24])[CH3:17])[N:10]=[C:9]([OH:14])[CH:8]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 524203081-[(1R)-1-chloroethyl]-2-fluorobenzeneHCID 178507962HCID 178507962, compound

Product 1

HCID 178462379HCID 178462379, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60% in oil, 1.05 g, 26.3 mmol) was added in portions followed by NaBH4 (0.099 g, 2.7 mmol) to 6-amino-2-mercaptopyrimidin-4-ol monohydrate (4.23 g, 26.3 mmol) in DMF (40 mL). After 30 minutes, 1-[(1R)-1-chloroethyl]-2-fluorobenzene (5.0 g, 31.5 mmol) in DMF (10 mL) was added and the reaction mixture was stirred for 24 h. The reaction mixture was concentrated and partitioned between water and DCM, the organic phase was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (a stepwise gradient of 5-10% MeOH in CHCl3) to give the title compound (5.20 g, 75% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between water and DCM
  3. dry with materialthe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography (a stepwise gradient of 5-10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-e12421c7d6e94cdaadf04bad9afeaa55
Source dataset
uspto-grants-2011_05
Patent number
US07947693B2

Reaction notes

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