Acetic Acid → HCID 58233974, compound

HRID 881281Notes

Reaction equation

HRID 881281 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.[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[CH3:31][C:32](O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[O:16]1[CH2:17][CH2:18][N:13]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:28]4[CH2:29][CH2:30][N:25]([C:20]5[N:21]=[CH:22][CH:23]=[CH:24][N:19]=5)[CH2:26][CH2:27]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:31]3[CH:32]=[N:21][C:20]([NH2:25])=[N:19][CH:24]=3)[N:3]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887471-(2-Pyrimidinyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58233974HCID 58233974, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (150 mg, 0.5 mmol) in 1,2-dichloroethane (2.5 mL) was added 1-(2-pyrimidyl)piperazine (110 μL, 0.7 mmol) and AcOH (30 μL, 0.5 mmol). After stirring 10 min at room temperature, Na(OAc)3BH (130 mg, 0.6 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. The resulting crude mixture was coupled using General Procedure A with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin2-amine to provide 138 after reverse phase HPLC purification (5 mg). MS (Q1) 491 (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-2d1ac349085b4c938e6a2b7437986705
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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