Sodium hydride → HCID 86603189, compound

HRID 1818963Notes

Reaction equation

HRID 1818963 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]([C:18]1[S:22][C:21]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:25])=[N:20][CH:19]=1)[CH2:6][O:7][Si:8]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:11])[CH3:10].Cl[C:38]1[C:39]2[S:46][CH:45]=[CH:44][C:40]=2[N:41]=[CH:42][N:43]=1>C1COCC1>[N:41]1[C:40]2[CH:44]=[CH:45][S:46][C:39]=2[C:38]([O:3][CH2:4][CH:5]([C:18]2[S:22][C:21]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=3)=[O:25])=[N:20][CH:19]=2)[CH2:6][O:7][Si:8]([CH:15]([CH3:16])[CH3:17])([CH:12]([CH3:13])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[N:43][CH:42]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 86603188HCID 86603188, compound

Product 1

HCID 86603189HCID 86603189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of NaH (0.12 mmol as a 60% oil dispersion) in THF (0.20 mL) was added a solution of compound 73.3 (0.04 mmol) in THF (1.0 mL) at room temperature. After stirring for 1 hour, 4-chlorothieno[3,2-d]pyrimidine (0.04 mmol) was added and the reaction mixture was heated at 60° C. for 1 hour. The reaction was cooled and quenched with the addition of saturated NH4Cl. The reaction mixture was extracted with EtOAc, dried and concentrated to give a residue that was purified by preparative TLC (20% hexanes in EtOAc) to afford 1-{5-[2-(thieno[3,2-d]pyrimidin-4-yloxy)-1-triisopropylsilanyloxymethyl-ethyl]-thiazol-2-yl}-3-(3-trifluoromethyl-phenyl)-urea (compound 73.4).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with the addition of saturated NH4Cl
  3. extractionThe reaction mixture was extracted with EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by preparative TLC (20% hexanes in EtOAc)

Sources & evidence

ORD record
ord-7a4e64d677b94a37941131cb61185eed
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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