Acetic Acid → HCID 58234055, compound

HRID 1365188Notes

Reaction equation

HRID 1365188 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]=[N: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][N:56]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58234055HCID 58234055, 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 following General Procedure A with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine to provide 158 after reverse phase HPLC purification (15 mg). MS (Q1) 457 (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-1363d159964a44fb8880ff7fba313b93
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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