Isobutylene oxide → 4-(4-Chloro-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol

HRID 249692Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C([Li])CCC.[CH3:20][C:21]1([O:24][CH2:23]1)[CH3:22]>O1CCCC1>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:3]=[C:2]([CH2:1][CH2:20][C:21]([CH3:23])([OH:24])[CH3:22])[N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Methyl-4-chloro-6-morpholino-pyrimidine (10.7 g; 50 mmol) was dissolved in tetrahydrofuran (200 mL). The reaction was chilled to −78° C. under an inert atmosphere. A solution of n-butyllithium in hexanes (25 mL, 2.5M, 62.50 mmol) was added, and the reaction mixture was stirred for thirty minutes. A solution of isobutylene oxide 6.6 mL, 75 mmol) was added, and the reaction was allowed to warm to room temperature while stirring overnight. The solvent was removed under reduced pressure, and the crude material was dissolved in methylene chloride (200 mL) and washed with saturated ammonium chloride (2×50 mL), dried with sodium sulfate, and evaporated to dryness. The compound was purified by column chromatography to give 4-(4-chloro-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol (6.2 g, 21.7 mmol).

Workup

temperatureto warm to room temperature
stirringwhile stirring overnight
customThe solvent was removed under reduced pressure
dissolutionthe crude material was dissolved in methylene chloride (200 mL)
washwashed with saturated ammonium chloride (2×50 mL)
dry with materialdried with sodium sulfate
customevaporated to dryness
customThe compound was purified by column chromatography

Sources & evidence

ORD record: ord-ad2ca6de8bad4d8198a80686b462a850
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863270B2

Reaction notes

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