Morpholine → 2-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine

HRID 41888

Reaction equation

HRID 41888 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,4-dichloro-thieno[3,2-d]pyrimidine 3, (8.68 g, 42.34 mmol), morpholine (8.11 mL, 2.2 eq.) and MeOH (150 mL) was stirred at room temperature for 1 h. The reaction mixture was then filtered, washed with water and MeOH, to yield 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 as a white solid (11.04 g, 100%). 1H NMR (400 MHz, d6-DMSO) 3.74 (4H, t, J=4.9 Hz), 3.90 (4H, t, J=4.9 Hz), 7.40 (1H, d, J=5.6 Hz), 8.30 (1H, d, J=5.6 Hz).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washwashed with water and MeOH

Sources & evidence

ORD record
ord-5d80cd9231304cf48adb75d60b1764b9
Source dataset
uspto-grants-2013_09
Patent number
US08536161B2

Linked notes

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