Water → HCID 58117100, compound

HRID 2066507Notes

Reaction equation

HRID 2066507 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[CH2:28][CH2:27][C:23]2([CH2:26][NH:25][CH2:24]2)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[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:25]3[CH2:26][C:23]4([CH2:27][CH2:28][N:20]([CH3:19])[CH2:21][CH2:22]4)[CH2:24]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 109971177-Methyl-2,7-diazaspiro[3.5]nonaneHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58117100HCID 58117100, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (72 mg, 0.254 mmol) in DCE (7 mL) was added 7-methyl-2,7-diaza-spiro[3.5]nonane (45 mg, 0.321 mmol). The mixture was stirred at RT for 10 min, then sodium triacetoxyborohydride (81 mg, 0.382 mmol) was added and stirring was continued for 3 h. To the reaction mixture was added water and the resulting solution was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted with 2 M NH3 in MeOH an concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a yellow oil (31 mg, 30%).

Workup

  1. stirringstirring
  2. waitwas continued for 3 h
  3. washThe cartridge was washed with MeOH
  4. washthe desired product was eluted with 2 M NH3 in MeOH
  5. concentrationan concentrated in vacuo
  6. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-ce92cd053b534372a07f274f23759769
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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