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Propargyl alcohol → 3-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-yn-1-ol

HRID 2098674
Notes
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Reaction equation

HRID 2098674 reaction equation
[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][C:9](I)=[CH:8][C:6]=2[N:7]=1.[CH2:18]([OH:21])[C:19]#[CH:20].C(N(CC)CC)C>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[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][C:9]([C:20]#[C:19][CH2:18][OH:21])=[CH:8][C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 866183933-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-yn-1-ol

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-6-iodo-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 19, prepared according to Example 12, (1.57 g), propargyl alcohol (288 μL), copper iodide (39 mg), bis(triphenylphosphine)palladium(II) chloride (146 mg), triethylamine (25 ml), and tetrahydrofuran (30 ml) were stirred under nitrogen for 10 days. The reaction mixture was then partitioned between chloroform and brine, the combined organics were then dried (MgSO4). The solvents were removed in vacuo. The crude product was then purified using flash chromatography to yield 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-yn-1-ol (1.2 g).

Workup

  1. customprepared
  2. customThe reaction mixture was then partitioned between chloroform and brine
  3. dry with materialthe combined organics were then dried (MgSO4)
  4. customThe solvents were removed in vacuo
  5. customThe crude product was then purified

Sources & evidence

ORD record
ord-adf33fcb00df4b3ab863397f80cac4c3
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450315B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes