Trimethyl orthoformate → HCID 58117084, compound

HRID 2066493Notes

Reaction equation

HRID 2066493 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[CH:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.Cl.Cl.[CH:21]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].COC(OC)OC>ClCCCl.ClCCl>[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[CH:10]=[C:9]([CH2:11][N:27]3[CH2:28][CH2:29][N:24]([CH:21]4[CH2:23][CH2:22]4)[CH2:25][CH2:26]3)[S:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 212208121-Cyclopropylpiperazine dihydrochlorideHCID 568338442-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58117084HCID 58117084, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-morpholin-4-yl-thieno[2,3-d]pyrimidine-6-carbaldehyde (254 mg), 1-cyclopropyl-piperazine di-HCl (264 mg), sodium triacetoxyborohydride (619 mg) and trimethylorthoformate (968 μL), was stirred in anhydrous 1,2-dichloroethane (25 mL) for 12 hours at room temperature, then diluted with dichloromethane (50 mL), and washed with 50% sodium bicarbonate solution. The organic phase was dried (MgSO4) and the solvents removed in vacuo to give a residue which was purified using flash silica chromatography to yield the title compound (217 mg) as a buff solid.

Workup

  1. washwashed with 50% sodium bicarbonate solution
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customto give a residue which
  5. customwas purified

Sources & evidence

ORD record
ord-29e655f92d2941038e52cdf8245e393e
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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