Lithium borohydride → [2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methanol
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]=1Participants
4
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
- temperatureto warm to room temperature
- customThe reaction was quenched with water (20 mL)
- customthen evaporated to dryness
- dissolutionThe residue was dissolved in ethyl acetate (150 mL)
- washwashed with water (150 mL)
- concentrationThe organics were concentrated in vacuo
Sources & evidence
- ORD record
- ord-ce81e909f6db4698a55b361641458147
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750003B2
Reaction notes
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