Dimethylformamide → 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide

HRID 2098692Notes

Reaction equation

HRID 2098692 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=[O:12])=[CH:8][C:6]=2[N:7]=1.[C:19](Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:30][O:31][CH2:32][CH2:33][NH2:34]>ClCCl.C(N(CC)CC)C>[CH3:30][O:31][CH2:32][CH2:33][NH:34][C:11]([C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([CH3:19])=[N:7][C:6]=2[CH:8]=1)=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80182-MethoxyethylamineHCID 65578Oxalyl chlorideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 671902602-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 in dichloromethane (2 ml) was added 2M oxalyl chloride solution in dichloromethane (0.75 ml) followed by 2 microdrops of dimethylformamide. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo to give a crude product. This crude product was stirred in dichloromethane (5 ml) and to it was added 2-methoxyethylamine (34.84) and triethylamine (61.5 μL). The reaction mixture was stirred at room temperature overnight. It was then partitioned between dichloromethane and saturated sodium bicarbonate solution, the combined organics were dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified by flash chromatography to yield 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide (30 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a crude product
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customIt was then partitioned between dichloromethane and saturated sodium bicarbonate solution
  5. dry with materialthe combined organics were dried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customto give a crude residue
  8. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-126ae28c6cab4d809a1f33e74705e76d
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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