Acetonitrile → HCID 9842334, compound

HRID 1838967Notes

Reaction equation

HRID 1838967 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([CH:16]=[O:17])=[C:4]([N:18](CC2C=CC(OC)=CC=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1.C1(CO)CCCCC1.C(#N)C>FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([CH:16]=[O:17])=[C:4]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7507CyclohexanemethanolHCID 12986176HCID 12986176, compound

Product 1

HCID 9842334HCID 9842334, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of 2-Amino-4-cyclohexylmethoxy-6-di(4-methoxybenzyl)amino-5-pyrimidine carbaldehyde and cyclohexylmethanol obtained previously was stirred in trifluoroacetic acid (2 ml) for 18 h. Excess trifluoroacetic acid was removed, and the residue extracted with ethyl acetate and water (50 ml each) Further ethyl acetate was added to the aqueous layer, and the organic components combined, dried and evaporated. The residual brown oil was applied to a silica column, eluting with 20% EtOAc/petrol (40:60). A pale yellow oil was obtained. Addition and removal of acetonitrile gave a solid which was recrystallised from a petrol/ethyl acetate mixture (0.091 g; 0.34 mmol) M.p. 97° C.

Workup

  1. customobtained previously
  2. customExcess trifluoroacetic acid was removed
  3. extractionthe residue extracted with ethyl acetate and water (50 ml each) Further ethyl acetate
  4. additionwas added to the aqueous layer
  5. customdried
  6. customevaporated
  7. washeluting with 20% EtOAc/petrol (40:60)
  8. customA pale yellow oil was obtained
  9. customgave a solid which

Sources & evidence

ORD record
ord-abd7b845c20a4648afb847c1497a87ea
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

Loading…