Triethylamine → Methanesulfonic acid 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-ethyl ester

HRID 881430Notes

Reaction equation

HRID 881430 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH:11]([OH:13])[CH3:12])=[CH:8][C:6]=2[N:7]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH:11]([O:13][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:12])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866184291-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-ethanol

Product 1

HCID 86618430Methanesulfonic acid 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-ethanol (509 mg) in dichloromethane (20 mL) at 0° C. was added triethylamine (0.28 mL) and then methanesulfonyl chloride (0.14 mL). The reaction mixture was stirred at room temperature for 16 h and then quenched with water and extracted into dichloromethane. The combined organics were washed with brine, dried (MgSO4) and reduced in vacuo to yield methanesulfonic acid 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-ethyl ester (640 mg).

Workup

  1. customquenched with water
  2. extractionextracted into dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-b4084dbc05954619bdb60cec3f3d3743
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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