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

HRID 390798Notes

Reaction equation

HRID 390798 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[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([Li])CCC.CCCCCC.CN([CH:31]=[O:32])C>C1COCC1>[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[CH:10]=[C:9]([CH:31]=[O:32])[S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 130381892-Chloro-4-(morpholin-4-yl)thieno(2,3-d)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 568338442-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-chloro-4-morpholinothieno[2,3-d]pyrimidine (1.75 g, 6.85 mmol) in dry THF (40 mL) at −78° C. was added a 2.5M solution of n-butyllithium (nBuLi) in hexane (3.3 mL, 1.2 eq.). After stirring for 1 h, dry DMF (796 μL, 1.5 eq.) was added. The reaction mixture was stirred for 1 h at −78° C. and then warmed slowly to room temperature. After a further 2 h 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 2-chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde (1.50 g) MS (Q1) 284 (M+).

Workup

  1. stirringThe reaction mixture was stirred for 1 h at −78° C.
  2. additionAfter a further 2 h 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-cc9c2121a4954f648d2ddaaeb06755d2
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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