Acetic Acid → 4-(2-Chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

HRID 888901Notes

Reaction equation

HRID 888901 reaction equation
[Cl:1][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]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[Cl:1][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][N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 574203384-(2-Chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholineYield 45%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (147 mg, 0.52 mmol), 1-methyl-piperazine (1.5 eq, 87 μL) and acetic acid (1.05 eq, 32 μL) in 1,2-dichloroethane (3 mL) was added sodium triacetoxyborohydride (1.1 eq, 121 mg) and then stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with saturated solution of sodium hydrogen carbonate, brine, separated and dried (MgSO4). The crude product was evaporated in vacuo and purified by chromatography to give the title compound as an off-white crystalline solid (51 mg, 45%).

Workup

  1. washwashed with saturated solution of sodium hydrogen carbonate, brine
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. customThe crude product was evaporated in vacuo
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-dd7ed49c7a7d4b27ae1a66b2a23f1904
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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