Sodium triacetoxyborohydride → 2-(4-Azetidin-1-ylpiperidin-1-ylmethyl)-5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

HRID 1919389Notes

Reaction equation

HRID 1919389 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[N:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[N:19]1([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:19]1([CH:23]2[CH2:28][CH2:27][N:26]([CH2:11][C:9]3[S:8][C:6]4[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:13]5[CH2:18][CH2:17][O:16][CH2:15][CH2:14]5)[C:5]=4[N:10]=3)[CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 231531094-(Azetidin-1-YL)piperidineHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Product 1

HCID 582349332-(4-Azetidin-1-ylpiperidin-1-ylmethyl)-5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidineYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carbaldehyde (308 mg, 1.08 mmol) in DCE (8 mL) was added 4-azetidin-1-ylpiperidine (166 mg, 1.19 mmol). The resulting mixture was stirred at RT for 10 min then sodium triacetoxyborohydride (297 mg, 1.40 mmol) was added and stirring was continued for 18 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH and concentrated in vacuo to give the title compound as an off-white solid (263 mg, 60%).

Workup

  1. stirringstirring
  2. waitwas continued for 18 h
  3. washwashed with MeOH
  4. washthen eluted with 2 M NH3 in MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9782fd45a61d40aeb82f751469df203f
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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