2-Morpholinoethylamine → 4-Chloro-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide

HRID 500756Notes

Reaction equation

HRID 500756 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11](Cl)=[O:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]([NH:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 594245464-Chlorothieno[3,2-d]pyrimidine-6-carbonyl chloride

Product 1

HCID 594244794-Chloro-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 22 (500 mg, 2.15 mmol) in anhydrous DCM (20 mL) at 0° C. under nitrogen was added 4-(2-aminoethyl)-morpholine (307 mg, 2.36 mmol). The reaction mixture was allowed to warm to the room temperature over 3 hours and was stirred for additional 14 hours, treated with saturated aqueous solution of NHCO3 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The residues was purified by flash chromatography on silica gel (eluents MeOH— DCM, 5:95, then 1:9) to afford the title compound 23 (458 mg, 65% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ(ppm): 9.13 (t, J=5.6 Hz, 1H), 9.08 (s, 1H), 8.32 (s, 1H), 3.60-3.54 (m, 4H), 3.44 (q, J=6.8 Hz, 2H), 2.54-2.48 (m, 2H), 2.46-2.40 (m, 4H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residues was purified by flash chromatography on silica gel (eluents MeOH— DCM, 5:95

Sources & evidence

ORD record
ord-ca847b94fd1e4068ac1392e51a842e9f
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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