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Lithium borohydride → [2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol

HRID 2353635
Notes
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Reaction equation

HRID 2353635 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1.[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59379939methyl 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate

Product 1

HCID 59380181[2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate (3.15 g) was dissolved in dry THF (20 mL) and cooled to 0° C. under nitrogen. To this is added dropwise a solution of lithium borohydride (2.0M in THF, 6.09 mL). The solution was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with water (20 mL) then evaporated to dryness. The residue was dissolved in ethyl acetate (150 mL) and washed with water (150 mL) followed by brine (50 mL). The organics were concentrated in vacuo to give to the desired compound (2.44 g) as white solid.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water (20 mL)
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  5. washwashed with water (150 mL)
  6. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-ce81e909f6db4698a55b361641458147
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07750003B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes