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

HRID 1805795Notes

Reaction equation

HRID 1805795 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:9]=[C:10](Cl)[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=1>>[Cl:7][C:8]1[N:9]=[C:10]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 122173242,4-Dichlorothieno[2,3-d]pyrimidine

Product 1

HCID 130381892-Chloro-4-(morpholin-4-yl)thieno(2,3-d)pyrimidineYield 88.3%

Procedure

Morpholine (85.1, 0.977 mol, 2.2 equiv.) was added to a solution of 2,4-dichlorothieno[2,3-d]pyrimidine 17 (91 g, 0.444 mol, 1.0 equiv.). The reaction mixture was stirred at ambient temperature for 1 h and the resulting slurry was filtered, rinsed with water (500 ml). The cake was dried in vacuum oven at 55° C. for 24 hours to give 442-chlorothieno[2,3-d]pyrimidin-4-yl)morpholine 18 as an off-white solid (100.3 g, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ 3.736 (t, J=4.8 Hz, 4H), δ 3.897 (t, J=5.2 Hz, 4H), δ 7.658 (d, J=6.4 Hz, 1H), δ 7.682 (t, J=6.4 Hz, 4H δ). LCMS (ESI pos) m/e 257 (M+1).

Workup

  1. filtrationthe resulting slurry was filtered
  2. washrinsed with water (500 ml)
  3. customThe cake was dried in vacuum oven at 55° C. for 24 hours

Sources & evidence

ORD record
ord-3ab10c97341f475ca3662f37f57db2a3
Source dataset
uspto-grants-2013_01
Patent number
US08354528B2

Reaction notes

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