Acetic Acid → HCID 86619261, compound

HRID 2403415Notes

Reaction equation

HRID 2403415 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[N:12]=[C:13]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:14]2[S:19][C:18]([CH:20]=O)=[CH:17][C:15]=2[N:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[Cl:10][C:11]1[N:12]=[C:13]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:14]2[S:19][C:18]([CH2:20][NH:1][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)=[CH:17][C:15]=2[N:16]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4082852-MorpholinoethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86619261HCID 86619261, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-(2-aminoethyl)-morpholine (600 mg) stirring in anhydrous 1,2-dichloroethane (40 ml), was added 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (1.31 g), followed by glacial acetic acid (277 μl) and sodium triacetoxy borohydride (1.27 g) added in several aliquots over 30 minutes. The reaction mixture was stirred for 12 hours at room temperature, then diluted with chloroform (50 ml), washed with 50% NaHCO3 solution and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash silica chromatography to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-ylmethyl)-(2-morpholin-4-yl-ethyl)-amine (398 mg), as a white solid.

Workup

  1. additionadded in several aliquots over 30 minutes
  2. washwashed with 50% NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. customThe solvents were removed in vacuo
  5. customto give a residue which
  6. customwas purified by flash silica chromatography

Sources & evidence

ORD record
ord-78b248be837b4a408bce3b109c61efe3
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

Loading…