Benzaldehyde → HCID 58234958, compound
Reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9]([CH3:11])[S:8][C:6]=2[N:7]=1.CN(C)CCN(C)C.[Li]CCCC.[CH:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9]([CH2:11][CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[OH:38])[S:8][C:6]=2[N:7]=1Participants
Procedure
To a solution of 5-chloro-2-methyl-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidine (1.33 g, 4.91 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.74 mL, 5.40 mmol) in anhydrous THF (50 mL) was added a solution of n-BuLi (2.5 M in hexanes, 2.4 mL, 6.0 mmol) dropwise at −78° C. The reaction mixture was stirred for 15 min, then a solution of benzaldehyde (0.65 mL, 6.29 mmol) in anhydrous THF (5 mL) was added rapidly. The mixture was stirred at −78° C. for 15 min, then allowed to warm to RT and partitioned between EtOAc and H2O. The organic layer was isolated, washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a yellow solid (1.20 g, 66%).
Workup
- stirringThe mixture was stirred at −78° C. for 15 min
- custompartitioned between EtOAc and H2O
- customThe organic layer was isolated
- washwashed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe resultant residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-79012ea431be48a59825ab174547be98
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168633B2
Reaction notes
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