Trimethyl orthoformate → HCID 86618380, compound

HRID 2098653Notes

Reaction equation

HRID 2098653 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]([CH2:11][CH:12]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[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]([CH2:11][CH2:12][N:27]3[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 7091611-(Methylsulfonyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86618381HCID 86618381, compound

Product 1

HCID 86618380HCID 86618380, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of crude (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-acetaldehyde (300 mg) and 1-methanesulfonyl-piperazine (243 mg) in 1,2-dichloroethane (10 mL) at room temperature was added trimethylorthoformate (0.33 mL). The reaction mixture was stirred at room temperature for 1 h and then sodium triacetoxyborohydride (534 mg) was added. The reaction mixture was stirred at room temperature for 16 h and then quenched with saturated aqueous sodium carbonate solution (20 mL) and extracted into dichloromethane (2×20 mL). The combined organics were washed with aqueous brine solution (2×20 mL), dried (MgSO4), concentrated and purified using column chromatography to give 2-chloro-6-[2-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a white solid (100 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customquenched with saturated aqueous sodium carbonate solution (20 mL)
  3. extractionextracted into dichloromethane (2×20 mL)
  4. washThe combined organics were washed with aqueous brine solution (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-0e0bd442fa76431e84da07ed906682d1
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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