1-Methyl-4-piperidone → HCID 86618402, compound

HRID 2098684Notes

Reaction equation

HRID 2098684 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:17]([Li])CCC.C[N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][C:9]([N:23]3[CH2:24][CH2:25][CH:26]([OH:29])[CH2:27][CH:28]3[CH3:17])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 86618402HCID 86618402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (288 mg) in anhydrous tetrahydrofuran (10 ml), with stirring at −78° C., was added 2.5M n-butyllithium in hexanes (541 μL). The reaction mixture was warmed gradually to −40° C. over 1 hour and then cooled to −78° C. 1-methyl-4-piperidone (138 μL) was then added. The reaction mixture was gradually warmed to room temperature and then left to stir for 3 days. The reaction mixture was then quenched with water the precipitate formed filtered. This crude product was then purified using flash chromatography to yield 1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-methyl-piperidin-4-ol (135 mg).

Workup

  1. temperaturecooled to −78° C
  2. temperatureThe reaction mixture was gradually warmed to room temperature
  3. waitleft
  4. customThe reaction mixture was then quenched with water the precipitate
  5. customformed
  6. filtrationfiltered
  7. customThis crude product was then purified

Sources & evidence

ORD record
ord-b00c23f3f38a455f899b32c05ed7c793
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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