Sodium triacetoxyborohydride → HCID 58117060, compound

HRID 2066473Notes

Reaction equation

HRID 2066473 reaction equation
[C:1]1(=[O:10])[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][NH:2]1.[Cl:11][C:12]1[N:13]=[C:14]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:15]2[S:20][C:19]([CH:21]=O)=[CH:18][C:16]=2[N:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:11][C:12]1[N:13]=[C:14]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[C:15]2[S:20][C:19]([CH2:21][N:7]3[CH2:8][CH2:9][C:4]4([C:1](=[O:10])[NH:2][CH2:3]4)[CH2:5][CH2:6]3)=[CH:18][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21692403HCID 21692403, compoundHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58117060HCID 58117060, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-oxo-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (150 mg, 0.624 mmol) in DCM (6 mL) was added TFA (3 mL) and the resulting solution stirred at RT for 1 h. The crude reaction mixture was loaded onto a Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH to provide 2,7-diaza-spiro[3.5]nonan-1-one as a colourless oil. To a suspension of 2,7-diaza-spiro[3.5]nonan-1-one (0.624 mmol) in dichloroethane (13 mL) were added 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (130 mg, 0.458 mmol) and sodium triacetoxyborohydride (146 mg, 0.689 mmol) and the resulting suspension stirred at RT for 18 h. The reaction was quenched with water and loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH. The resulting residue was then purified by column chromatography to give the title compound as a white solid (93 mg, 50%)

Workup

  1. customThe reaction was quenched with water
  2. washwashed with MeOH
  3. washthen eluted with 2 M NH3 in MeOH
  4. customThe resulting residue was then purified by column chromatography

Sources & evidence

ORD record
ord-fe1ff3aaedbc47149df6011d548ca040
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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