Acetic Acid → HCID 58233865, compound

HRID 390869Notes

Reaction equation

HRID 390869 reaction equation
Cl[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.[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC1(C)C(C)(C)OB([C:54]2[CH:55]=[CH:56][C:57]([NH2:60])=[N:58][CH:59]=2)O1>ClCCCl>[NH2:60][C:57]1[N:58]=[CH:59][C:54]([C:2]2[N:3]=[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:5]3[S:10][C:9]([CH2:11][N:25]4[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][OH:19])[CH2:23][CH2:24]4)=[CH:8][C:6]=3[N:7]=2)=[CH:55][CH:56]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58233865HCID 58233865, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (1.3 g, 4.6 mmol) in 1,2-dichloroethane (45 mL) was added 1-(2-hydroxyethyl)piperazine (0.8 mL, 6.4 mmol) and AcOH (260 μL, 4.6 mmol). After stirring 10 min at room temperature, Na(OAc)3BH (1.2 g, 5.5 mmol) was added and the resulting mixture stirred overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3 and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. A portion (0.4 mmol) of the crude intermediate was coupled using General Procedure A with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine to provide 157 after reverse phase HPLC purification (21 mg). MS (Q1) 456 (M)+.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customThe reaction was quenched by the addition of saturated aqueous NaHCO3
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab33dd00571640f48303aeb50d346aaa
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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