2-Bromoethanol → HCID 178491847, compound

HRID 1435335Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][CH2:28][CH2:29][OH:30])[CH2:23][CH2:22]2)[N:3]=1.Br[CH2:32][CH2:33][OH:34].C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([N:27]([CH2:32][CH2:33][OH:34])[CH2:28][CH2:29][OH:30])[CH2:23][CH2:22]2)[N:3]=1

Participants

Conditions

Temperature: 113 °C

Procedure

To a stirred solution of trans-[4-amino-2-[4-(2-hydroxy-ethylamino)-cyclohexylamino]-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (106 mg, 0.25 mmol, Example 120) in 1,4-dioxane (3 mL), 2-bromoethanol (80 uL, 1.12 mmol, Aldrich) and sodium bicarbonate (50 mg, 0.60 mmol) were added and the mixture was heated at 113° C. for 24 hours. The reaction was quenched with water and the mixture was extracted with ethyl acetate (3×10 mL) and the extracts were dried with sodium sulfate. The solvent was removed and the residue was chromatographed (8% 9N ammonia in methanol/dichloromethane) to give a pale yellow solid. 97 mg, 84%. MS (ES) MH+=466.

Workup

customThe reaction was quenched with water
extractionthe mixture was extracted with ethyl acetate (3×10 mL)
dry with materialthe extracts were dried with sodium sulfate
customThe solvent was removed
customthe residue was chromatographed (8% 9N ammonia in methanol/dichloromethane)
customto give a pale yellow solid

Sources & evidence

ORD record: ord-e4afd068e0a64d49ab3cc5b377d7bcbc
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615634B2

Reaction notes

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