Triethylamine → 2-Chloro-6-(7-methanesulfonyl-2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066513Notes

Reaction equation

HRID 2066513 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:15][C:14]4([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[CH2:13]3)=[CH:8][C:6]=2[N:7]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:13][C:14]4([CH2:20][CH2:19][N:18]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:17][CH2:16]4)[CH2:15]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 581171422-Chloro-6-(2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 581171302-Chloro-6-(7-methanesulfonyl-2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-chloro-6-(2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (71 mg, 0.18 mmol) in anhydrous DCM (3 mL) was added triethylamine (160 μL, 1.46 mmol) and a solution of methanesulfonyl chloride (17 μL, 0.22 mmol) in anhydrous DCM (0.5 mL). The resulting mixture was stirred at RT for 18 h, then diluted with DCM and brine. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a yellow oil (55 mg, 65%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-1de45f775a164a4a9cb3c8e83a5961a5
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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