Sodium Hydroxide → HCID 66779840, compound

HRID 1958027Notes

Reaction equation

HRID 1958027 reaction equation
C([Mg]Cl)(C)C.[N:6]1([C:12]2[S:13][C:14]3[C:19](=[O:20])[N:18]=[CH:17][NH:16][C:15]=3[N:21]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.BrC[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[C:35]=1[CH3:44].[OH-].[Na+]>O1CCCC1.O.CO>[CH3:44][C:35]1[C:36]([C:40]([F:41])([F:42])[F:43])=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:17][NH:16][C:15]1[N:21]=[C:12]([N:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[S:13][C:14]=1[C:19]([NH2:18])=[O:20]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 2733832Lithium HexamethyldisilazideHCID 27756171-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzeneHCID 178418918HCID 178418918, compoundHCID 178518229HCID 178518229, compound

Product 1

HCID 66779840HCID 66779840, compoundYield 117.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isopropylmagnesium chloride (1.679 mL, 3.36 mmol) was added to a suspension of 2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (0.8 g, 3.36 mmol) in Tetrahydrofuran (THF) (30 mL) at 0° C. LiHMDS (3.36 mL, 3.36 mmol) was added. The ice bath was removed. The reaction mixture was stirred at RT for 30 min, cooled down to 0° C. 1-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (1 g, 3.95 mmol) was added. The reaction mixture was heated at 60 C overnight. LCMS showed very clean reaction. NaOH (1.12 mL, 6.72 mmol, 6N) was added. The resulting mixture was heated at 60° C. for 1 hr (MeOH may be added to accelerate the reaction). LCMS showed the hydrolysis was almost complete. Water was added, creamy-colored solid was formed, filtered, rinsed with water, and dried under high vacuum at 50° C. to give 1.58 g of product, which may contain inorganic salt.

Workup

  1. customThe ice bath was removed
  2. temperaturecooled down to 0° C
  3. temperatureThe reaction mixture was heated at 60 C overnight
  4. customreaction
  5. additionmay be added
  6. customthe reaction)
  7. customcreamy-colored solid was formed
  8. filtrationfiltered
  9. washrinsed with water
  10. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-c0095a674dee49c6a6d2b2a1c0ed9604
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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