Potassium tert-butoxide → HCID 178433337, compound

HRID 472214Notes

Reaction equation

HRID 472214 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[C:5](/[CH:16]=[CH:17]/[C:18](OCC)=[O:19])=[C:4]([CH3:23])[N:3]=1.CC(C)([O-])C.[K+]>CC(N(C)C)=O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:23])[C:5]2[CH:16]=[CH:17][C:18](=[O:19])[N:8]([C@H:9]3[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471088HCID 178471088, compound

Product 1

HCID 178433337HCID 178433337, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (E)-ethyl 3-(2-amino-4-(trans-4-hydroxycyclohexylamino)-6-methylpyrimidin-5-yl)acrylate (233 mg, 0.727 mmol) in dimethylacetamide was added 1,5-diazbicyclo[5,4,0]undec-5-ene (544 uL, 3.64 mmol) followed by potassium tert-butoxide (1 M in THF, 364 uL, 364 mmol). The resulting solution was heated at 150° C. overnight then concentrated. The residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-5%). The product was then triturated with 1:1 chloroform:hexane to afford the title compound (119 mg, 60%).

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with chloroform/7 N ammonia in methanol (0.5-5%)
  4. customThe product was then triturated with 1:1 chloroform

Sources & evidence

ORD record
ord-9a7252c5f5af41469ceb27f889f6e5a0
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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