Dimethylformamide → 2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

HRID 888900Notes

Reaction equation

HRID 888900 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Li]CCCC.CN(C)[CH:24]=[O:25]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][C:9]([CH:24]=[O:25])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (1.75 g, 6.85 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added nBuLi (3.3 mL, 1.2 equivalents, 2.5 M solution in hexanes). After stirring for 1 hour, dry N,N-dimethylformamide (796 μL, 1.5 equivalents) was added. The reaction mixture was stirred for 1 hour at −78° C. and then warmed slowly to room temperature. After a further 2 hours at room temperature the reaction mixture was poured onto ice-water yielding a yellow precipitate. This was collected by filtration and air-dried to yield the title compound (1.50 g, 77%).

Workup

  1. stirringThe reaction mixture was stirred for 1 hour at −78° C.
  2. additionAfter a further 2 hours at room temperature the reaction mixture was poured onto ice-water yielding a yellow precipitate
  3. filtrationThis was collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-96486ebd77324f24873b1c110ec21968
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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