Lithium Hydroxide → (2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol

HRID 2091831Notes

Reaction equation

HRID 2091831 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]([Cl:22])[N:12]=[C:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:14]=2[N:15]=1)(=O)C.[OH-].[Li+]>C1COCC1.O>[Cl:22][C:11]1[N:12]=[C:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[C:14]2[N:15]=[C:6]([CH2:5][OH:4])[CH:7]=[CH:8][C:9]=2[N:10]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86657075(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl acetate

Product 1

HCID 53488008(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl acetate 5 (2.3 g, 7.1 mmol) in THF (50 mL) was added a 1M solution of lithium hydroxide in water (26 mL). The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted three times with dichloromethane. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol 6. LCMS (MH)+=281.1. 1H-NMR (400 MHz, CDCl3, ppm): 8.09 (1H, d, J=8.8 Hz), 7.66 (1H, d, J=8.8 Hz), 4.91 (2H, s), 4.56 (4H, br), 3.91 (4H, t), 2.86 (1H, s)

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b673ca2c933047c58e27c080b90cc75e
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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