Acetic Acid → HCID 178480811, compound

HRID 253023Notes

Reaction equation

HRID 253023 reaction equation
[N:1]1([C:7]2[C:8]3[S:30][C:29]([CH:31]=O)=[CH:28][C:9]=3[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][SiH2:20][C:21]([CH3:27])([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:14]=3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([CH2:31][C:29]2[S:30][C:8]3[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[N:12][C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19][SiH2:20][C:21]([CH3:26])([CH3:27])[C:22]([CH3:25])([CH3:23])[CH3:24])[CH:14]=4)=[N:10][C:9]=3[CH:28]=2)[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 137329915HCID 137329915, compound

Product 1

HCID 178480811HCID 178480811, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-morpholin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine-6-carbaldehyde (6.67 g, 14.66 mmol), N-methylpiperazine (2.11 mL, 1.3 equivalents) and acetic acid (838 μL, 1.0 eq.) was stirred in 1,2-dichloroethane (70 mL) at room temperature. To this was added sodium triacetoxyborohydride (3.42 g, 1.1 equivalents) and the reaction mixture was stirred for 3 days. The reaction mixture was then quenched with aqueous sodium bicarbonate solution, extracted exhaustively with chloroform, dried (MgSO4), and the solvent removed in vacuo to yield a yellow oil. This was purified using flash chromatography (silica, ethyl acetate to ethyl acetate/methanol) to yield 6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine (6.95 g, 88%).

Workup

  1. customThe reaction mixture was then quenched with aqueous sodium bicarbonate solution
  2. extractionextracted exhaustively with chloroform
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto yield a yellow oil
  6. customThis was purified

Sources & evidence

ORD record
ord-1a977a598b2d40f082a068ec1af8ee46
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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