Triethylamine → HCID 86618377, compound

HRID 2098649Notes

Reaction equation

HRID 2098649 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][OH:12])=[CH:8][C:6]=2[N:7]=1.[CH2:19](N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:19][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][O:12][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Product 1

HCID 86618377HCID 86618377, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methanol (500 mg) and triethylamine (0.5 mL) in dichloromethane (20 mL) at 0° C. was added methanesulfonyl chloride (0.27 mL). The reaction mixture was stirred at room temperature for 16 h and then quenched with water (20 mL) and extracted into dichloromethane (2×20 mL). The combined organics were washed with aqueous brine solution (2×20 mL), dried (MgSO4) and concentrated to give methanesulfonic acid 2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl ester as a yellow solid (523 mg).

Workup

  1. customquenched with water (20 mL)
  2. extractionextracted into dichloromethane (2×20 mL)
  3. washThe combined organics were washed with aqueous brine solution (2×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d71cd884430942c9b5bc9d35646b309f
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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