Acetic Acid → HCID 86619262, compound

HRID 2403417Notes

Reaction equation

HRID 2403417 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.[CH3:19][O:20][CH2:21][CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1.C(O)(=O)C.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[S:10][C:9]([CH2:11][N:23]([CH2:22][CH2:21][O:20][CH3:19])[CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2761027N-(2-methoxyethyl)-1-methylpiperidin-4-amineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86619262HCID 86619262, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (150 mg) and (2-methoxy-ethyl)-(1-methyl-piperidin-4-yl)-amine (128 mg) were stirred together in 1,2-dichloroethane (8 ml) and acetic acid (32 mg) with sodium triacetoxyborohydride (146 mg) at room temperature overnight. Dichloromethane/aqueous sodium hydrogen carbonate extraction and purification on silica yielded (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(2-methoxy-ethyl)-(1-methyl-piperidin-4-yl)-amine (97 mg).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionDichloromethane/aqueous sodium hydrogen carbonate extraction and purification on silica

Sources & evidence

ORD record
ord-768953e5ab3d4e24b7463f0baf723a88
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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