Triethylamine → HCID 86618413, compound

HRID 2262145Notes

Reaction equation

HRID 2262145 reaction equation
Cl.Cl.[Cl:3][C:4]1[N:5]=[C:6]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:7]2[S:12][C:11]([C:13]3([OH:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:10][C:8]=2[N:9]=1.[S:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:3][C:4]1[N:5]=[C:6]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:7]2[S:12][C:11]([C:13]3([OH:19])[CH2:14][CH2:15][N:16]([CH2:31][C:27]4[S:26][CH:30]=[CH:29][N:28]=4)[CH2:17][CH2:18]3)=[CH:10][C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86618414HCID 86618414, compound

Product 1

HCID 86618413HCID 86618413, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)piperidin-4-ol dihydrochloride salt (250 mg) and 2-thiazole-carboxaldehyde (0.08 ml) were stirred together in 1,2-dichloroethane (3 ml) and triethylamine (0.18 ml) with sodium triacetoxyborohydride (187 mg) at room temperature overnight. Dichloromethane/brine extraction and purification on silica yielded 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-1-thiazol-2-ylmethyl-piperidin-4-ol (119 mg).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionDichloromethane/brine extraction and purification on silica

Sources & evidence

ORD record
ord-aaea185ba7624217bc5571869e68811d
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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