Sodium borohydride → 1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

HRID 2098699Notes

Reaction equation

HRID 2098699 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]=[N:12]/[CH3:13])=[CH:8][C:6]=2[N:7]=1.[BH4-].[Na+]>CO.O1CCCC1>[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][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178482580HCID 178482580, compound

Product 1

HCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamineYield 37.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To [1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-meth-(E)-ylidene]-methyl-amine (0.9 g) in methanol (25 ml) and tetrahydrofuran (10 ml) under nitrogen was added sodium borohydride (0.17 g) and molecular sieves. The reaction mixture was stirred at room temperature overnight. The solvents were removed in vacuo, quenched with brine, extracted with dichloromethane, dried (MgSO4) and the solvent removed in vacuo to give a crude product which was purified using flash chromatography to give (2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-amine (342 mg).

Workup

  1. customThe solvents were removed in vacuo
  2. customquenched with brine
  3. extractionextracted with dichloromethane
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a crude product which
  7. customwas purified

Sources & evidence

ORD record
ord-f923b3e84b094ede83dd8c9149ab1b0a
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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