Tetrahydrofuran → HCID 18009132, compound

HRID 987545Notes

Reaction equation

HRID 987545 reaction equation
C([C:5]1[CH:33]=[CH:32][C:8]([N:9](O[SiH](C)C)[C:10]2[CH:15]=[C:14]([N:16]([CH2:25][C:26]#[N:27])[C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[Br:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1)(C)(C)C.[F-].[O:35]1CCCC1>>[OH:35][C:5]1[CH:33]=[CH:32][C:8]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:25][C:26]#[N:27])[C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[Br:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 28179Fluoride IonHCID 131724089HCID 131724089, compound

Product 1

HCID 18009132HCID 18009132, compoundYield 73%

Procedure

To a solution of 4-(4-tertbutyldimethylsilyloxyanilino)-6-(N-cyanomethyl-2-bromo-4-methylanilino)pyrimidine (Reference Example 2, 890 mg) in tetrahydrofuran (1 ml) was added N,N,N,N-tetraburylammonium fluoride (1M solution in tetrahydrofuran, 2 ml). The reaction mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated and the residue partitioned between EtOAc and water. The organic layer was separated and dried (MgSO4), evaporated and purified by column chromatography eluting with DCM:MeOH:concentrated ammonia; 95:4:1 to give the title compound (510 mg, 73%) as a solid. M/z 410 (MH+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurified by column chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-4c47dd194c6b491a9478ff680d9b4e6a
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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