Sodium triacetoxyborohydride → 4-[1-(5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-ylmethyl)azetidin-3-yl]piperazin-2-one

HRID 1922774Notes

Reaction equation

HRID 1922774 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.[NH:19]1[CH2:22][CH:21]([N:23]2[CH2:28][CH2:27][NH:26][C:25](=[O:29])[CH2:24]2)[CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>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[N:10]=[C:9]([CH2:11][N:19]3[CH2:20][CH:21]([N:23]4[CH2:28][CH2:27][NH:26][C:25](=[O:29])[CH2:24]4)[CH2:22]3)[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehydeHCID 596061454-(Azetidin-3-yl)piperazin-2-one

Product 1

HCID 596052704-[1-(5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-ylmethyl)azetidin-3-yl]piperazin-2-oneYield 75.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carbaldehyde (285 mg, 1.00 mmol), 4-azetidin-3-ylpiperazin-2-one (190 mg, 1.22 mmol) and 4 Å powdered molecular sieves (1.0 g) in DCE (10 mL) was allowed to stir at r.t. for 5 h before the addition of sodium triacetoxyborohydride (420 mg, 1.98 mmol). The resulting mixture was allowed to stir for 16 h then filtered through Celite® which was washed with DCM. The filtrate was concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 2-10%) affording the title compound (321 mg, 75%)._LCMS (method A): RT 1.96 and 0.33 min [M+H]+ 424.3

Workup

  1. filtrationthen filtered through Celite® which
  2. washwas washed with DCM
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 2-10%)

Sources & evidence

ORD record
ord-d159f01a57564d82bef48819351c88b8
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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