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

HRID 1972312Notes

Reaction equation

HRID 1972312 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[S:16][CH:15]=[CH: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[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

3

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 94%

Procedure

Morpholine (87 ml, 1.00 mol, 2.2 equiv.) was added to a solution of 2,4-dichloro-thieno[3,2-d]pyrimidine 3 (93.4 g, 0.456 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 a vacuum oven at 40° C. for 24 hours to give 4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine 4 as an off-white solid (109 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ 3.74 (t, J=4.9 Hz, 4H), 3.90 (t, J=4.9 Hz, 4H), 7.40 (d, J=5.6 Hz, 1H), 8.30 (d, J=5.6 Hz, 1H). 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 a vacuum oven at 40° C. for 24 hours

Sources & evidence

ORD record
ord-1b25c5dfabd141498c4e0f688773b35b
Source dataset
uspto-grants-2013_04
Patent number
US08431694B1

Reaction notes

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