Acetic Acid → HCID 59603423, compound

HRID 1945619Notes

Reaction equation

HRID 1945619 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH:11]=O)=[C:8]([CH3:13])[C:6]=2[N:7]=1.[N:20]1([C:26]([CH3:31])([CH3:30])[C:27]([NH2:29])=[O:28])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(OC)(OC)OC.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:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][N:23]3[CH2:22][CH2:21][N:20]([C:26]([CH3:31])([CH3:30])[C:27]([NH2:29])=[O:28])[CH2:25][CH2:24]3)=[C:8]([CH3:13])[C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 217488412-Methyl-2-(piperazin-1-yl)propanamideHCID 566485822-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 59603423HCID 59603423, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (1.00 g, 3.36 mmol) in DCE (50 mL) was added 2-(piperazin-1-yl)isobutyramide (630 mg, 3.69 mmol), trimethyl orthoformate (3.67 mL, 33.58 mmol) and acetic acid (0.19 mL, 3.36 mmol). After stirring at room temperature for 3 h sodium triacetoxyborohydride (1.10 g, 5.03 mmol) was added and the resulting mixture stirred for a further 17 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH/DCM. The resultant residue was triturated with MeOH to give 2-[4-(2-Chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramide as a white solid (1.12 g, 74%). LCMS (Method C): RT=2.88 min, [M+H]+ 453

Workup

  1. additionwas added
  2. washwashed with MeOH
  3. washthen eluted with 2 M NH3 in MeOH/DCM
  4. customThe resultant residue was triturated with MeOH

Sources & evidence

ORD record
ord-ae2a090219c0482ab3fbf38d717bd876
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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