Triethylamine → Methanesulfonic acid 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-ynyl ester

HRID 2262099Notes

Reaction equation

HRID 2262099 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([C:11]#[C:12][CH2:13][OH:14])=[CH:8][C:6]=2[N:7]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([C:11]#[C:12][CH2:13][O:14][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866183933-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-yn-1-ol

Product 1

HCID 86618394Methanesulfonic acid 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-ynyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-yn-1-ol (142 mg) in chloroform (10 ml) was added triethylamine (77 μL) and methanesulfonyl chloride (49 μL). Stir at room temperature for 2 hours then partition between chloroform and brine, the combined organics were dried (MgSO4). The solvents were removed in vacuo to yield methanesulfonic acid 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-prop-2-ynyl ester (150 mg).

Workup

  1. customthen partition between chloroform and brine
  2. dry with materialthe combined organics were dried (MgSO4)
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-b41e0505904a425e97ca56e542010da7
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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