Dimethylformamide → HCID 137329915, compound

HRID 253022Notes

Reaction equation

HRID 253022 reaction equation
[N:1]1([C:7]2[C:8]3[S:30][CH:29]=[CH:28][C:9]=3[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][SiH2:20][C:21]([CH3:27])([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:14]=3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Li]CCCC.CN(C)[CH:38]=[O:39]>C1COCC1>[N:1]1([C:7]2[C:8]3[S:30][C:29]([CH:38]=[O:39])=[CH:28][C:9]=3[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][SiH2:20][C:21]([CH3:27])([CH3:26])[C:22]([CH3:24])([CH3:25])[CH3:23])[CH:14]=3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 137329916HCID 137329916, compoundHCID 178418339Butyllithium

Product 1

HCID 137329915HCID 137329915, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-morpholin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine (2.26 g, 5.29 mmol) in dry THF (40 mL) cooled to −78° C. was added nBuLi (2.5 M solution in hexanes, 2.75 mL, 1.3 eq.). After stirring for 20 minutes, dry N,N-dimethylformamide (617 μL, 1.5 eq.) was added, and the reaction mixture was stirred for 20 minutes at −78° C. and then warmed slowly to room temperature. After a further 30 minutes at room temperature the reaction mixture was quenched with ice/brine and then extracted exhaustively with chloroform. The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to yield compound 8 as a yellow solid (2.38 g, 99%).

Workup

  1. stirringthe reaction mixture was stirred for 20 minutes at −78° C.
  2. customAfter a further 30 minutes at room temperature the reaction mixture was quenched with ice/brine
  3. extractionextracted exhaustively with chloroform
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-df55bedd9c8245879f447415fa7f4012
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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