Sodium triacetoxyborohydride → 4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl ester

HRID 2066470Notes

Reaction equation

HRID 2066470 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.[C:19]([O:23][C:24]([N:26]1[CH2:36][CH2:35][C:29]2([O:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH2:28][C:29]2([O:34][CH2:33][CH2:32][N:31]([CH2:11][C:9]3[S:10][C:5]4[C:4]([N:13]5[CH2:18][CH2:17][O:16][CH2:15][CH2:14]5)=[N:3][C:2]([Cl:1])=[N:7][C:6]=4[CH:8]=3)[CH2:30]2)[CH2:35][CH2:36]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 53302318tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 581171354-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl esterYield 53.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (100 mg, 0.352 mmol) in dichloroethane (10 mL) were added 1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl ester (110 mg, 0.376 mmol) and sodium triacetoxyborohydride (113 mg, 0.533 mmol) and the resulting solution stirred at RT for 3 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 (98 mg, 53%) [M+H]+ 524.3

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-5f30f9eb1347455fb63655d48b7332a9
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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