Formaldehyde → HCID 58405007, compound

HRID 2091894Notes

Reaction equation

HRID 2091894 reaction equation
C=O.[Cl:3][C:4]1[N:5]=[C:6]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:7]2[N:13]=[C:12]([CH2:14][NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH:11]=[CH:10][C:8]=2[N:9]=1.[C:27]([BH3-])#N.[Na+].CO>C(Cl)Cl.C(OCC)(=O)C>[Cl:3][C:4]1[N:5]=[C:6]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:7]2[N:13]=[C:12]([CH2:14][N:15]([CH3:27])[CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 58405026HCID 58405026, compound

Product 1

HCID 58405007HCID 58405007, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Paraformaldehyde (20 mg, 1.5 eq) was added to a solution of 1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylamino)-2-methylpropan-2-ol (0.16 g) in DCM (2.5 mL). The reaction was stirred for 5 minutes before addition of sodium cyanoborohydride (1.2 eq). Methanol (1 mL) was added to the reaction mixture which was then stirred overnight at room temperature. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated to give 0.12 g of 1-(((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)-2-methylpropan-2-ol as a yellow oil.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89627f6b0ec549d9a3e8afdd3d6688aa
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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