2-Amino-2-methyl-1-propanol → HCID 11774467, compound

HRID 2353312Notes

Reaction equation

HRID 2353312 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:18](=[O:19])[N:17]([CH2:20][C@H:21]([OH:23])[CH3:22])[C:8]2[N:9]=[C:10](S(C)(=O)=O)[N:11]=[CH:12][C:7]=2[CH:6]=1.[NH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32]>>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:18](=[O:19])[N:17]([CH2:20][C@H:21]([OH:23])[CH3:22])[C:8]2[N:9]=[C:10]([NH:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32])[N:11]=[CH:12][C:7]=2[CH:6]=1

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 59681432HCID 59681432, compound

Product 1

HCID 11774467HCID 11774467, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(2,4-difluorophenoxy)-8-((R)-2-hydroxypropyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one (886 mg, 2.15 mmol) and 2-amino-2-methyl-1-propanol (5.15 g, 58 mmol) was heated at 60° C. under nitrogen for 2 hours. Cooled and chromatographed on silica gel eluding with 2% methanol in dichloromethane to give after converting to hydrochloride salt 385 mg 6-(2,4-Difluorophenoxy)-2-(2-hydroxy-1,1-dimethyl-ethylamino)-8-((R)-2-hydroxy-propyl)-8H-pyrido[2,3-d]pyrimidin-7-one (mass spec. M+1=421, MP=182.0-183.9° C.).

Workup

  1. temperatureCooled
  2. customchromatographed on silica gel eluding with 2% methanol in dichloromethane
  3. customto give

Sources & evidence

ORD record
ord-cc2081be10d0477baaf325fbf5ec8de3
Source dataset
uspto-grants-2010_07
Patent number
US07750016B2

Reaction notes

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