Tetrahydrofuran → 5-Bromo-N-(pyrimidin-4-YL)-N-((2-(trimethylsilyl)ethoxy)methyl)naphthalene-2-sulfonamide

HRID 1473364Notes

Reaction equation

HRID 1473364 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3][CH:2]=1.[CH3:8][Si:9]([CH2:12][CH2:13][O:14][CH2:15]Cl)([CH3:11])[CH3:10].[Br:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([S:28](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:30])=[O:29])=[CH:23]2.CC(C)([O-])C.[Li+].C1COCC1>CN(C=O)C>[Br:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([S:28]([N:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][N:3]=1)[CH2:15][O:14][CH2:13][CH2:12][Si:9]([CH3:11])([CH3:10])[CH3:8])(=[O:29])=[O:30])=[CH:23]2

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 689584-AminopyrimidineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 86687354Perfluorophenyl 5-bromonaphthalene-2-sulfonate2×

Product 1

HCID 866874115-Bromo-N-(pyrimidin-4-YL)-N-((2-(trimethylsilyl)ethoxy)methyl)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of pyrimidin-4-amine (0.944 g, 9.93 mmol) in 10 mL DMF was treated with SEM-Cl (1.761 ml, 9.93 mmol) and was allowed to stir at room temperature 30 minutes. Perfluorophenyl 5-bromonaphthalene-2-sulfonate (INTERMEDIATE M; 4.50 g, 9.93 mmol) was added and the reaction mixture was treated with lithium tert-butoxide 1N in THF (19.86 ml, 19.86 mmol) drop wise. After stirring for one hour, the reaction mixture was concentrated. The crude residue was diluted with DCM, washed with water, the organics dried over MgSO4 and concentrated. The material (INTERMEDIATE CCC) was carried forward crude without further purification.

Workup

  1. stirringAfter stirring for one hour
  2. concentrationthe reaction mixture was concentrated
  3. additionThe crude residue was diluted with DCM
  4. washwashed with water
  5. dry with materialthe organics dried over MgSO4
  6. concentrationconcentrated
  7. customwithout further purification

Sources & evidence

ORD record
ord-ced9276fac1948328149ad3fe9cf87f4
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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