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Ethanol → 4-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)morpholine

HRID 928577
Notes
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Reaction equation

HRID 928577 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C.C(O)C>>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 8471TriethylamineHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

Product 1

HCID 820658184-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)morpholine

Conditions

Temperature
50 °C

Procedure

2,4-Dichloro-5-phenyl-thieno[2,3-d]pyrimidine (2 g, 7.112 mmol), morpholine (0.9294 g, 10.67 mmol) and triethylamine (1.454 g, 2.00 mL, 14.22 mmol) were combined in ethanol (23.7 g, 30 mL, 493 mmol) and heated to 50° C. for 1 hour. The reaction mixture was allowed to cool to room temperature. The solvent volume was reduced by half and the resulting precipitate filtered off and washed with water and dried in vacuo overnight at 40° C. to afford 4-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)morpholine as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting precipitate filtered off
  3. washwashed with water
  4. customdried in vacuo overnight at 40° C.

Sources & evidence

ORD record
ord-39e52fc9d0bc49cbb12f0b778a7e8544
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290511B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes