Cesium carbonate → 8-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane

HRID 2066467Notes

Reaction equation

HRID 2066467 reaction equation
Br[CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([Cl:18])=[N:6][C:5]=2[CH:4]=1.[O:19]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:18][C:7]1[N:8]=[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]2[S:11][C:3]([CH2:2][N:26]3[CH2:27][CH2:28][C:23]4([O:22][CH2:21][CH2:20][O:19]4)[CH2:24][CH2:25]3)=[CH:4][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 581170818-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decaneYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (1.00 g, 2.87 mmol) in DMF (20 mL) were added 1,4-dioxa-8-aza-spiro[4.5]decane (1.06 mL, 8.62 mmol) and cesium carbonate (1.8 g, 5.75 mmol). The resulting mixture was stirred at RT for 90 min. The reaction mixture was diluted with water then extracted with EtOAc. The organic extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as an orange solid (0.97 g, 82%).

Workup

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-229384cf59984a69b88ec5009efd41e9
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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