Acetonitrile → Allyl [(4-amino-5-benzyl-2-pyrimidinyl)sulfanyl]acetate

HRID 722080Notes

Reaction equation

HRID 722080 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][N:5]=[C:4]([S:15][CH2:16][C:17]([OH:19])=[O:18])[N:3]=1.[CH:20]1(N=C=NC2CCCCC2)[CH2:25]CCC[CH2:21]1.C(O)C=C.CC#N>CN(C=O)C.CN(C)C1C=CN=CC=1.C(O)(C(F)(F)F)=O>[CH2:25]([O:18][C:17](=[O:19])[CH2:16][S:15][C:4]1[N:3]=[C:2]([NH2:1])[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][N:5]=1)[CH:20]=[CH2:21]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 7858Allyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 21883178(4-Amino-5-benzyl-pyrimidin-2-ylsulfanyl)-acetic acid

Product 1

HCID 9796950Allyl [(4-amino-5-benzyl-2-pyrimidinyl)sulfanyl]acetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(4-Amino-5-benzyl-pyrimidin-2-ylsulfanyl)-acetic acid (0.25 mmol, 69 mg), dicyclohexylcarbodiimide (0.3 mmol, 62 mg) and allyl alcohol (0.3 mmol, 18 mg) were dissolved in 1 ml of DMF, and a catalytic amount of 4-dimethylaminopyridine (approx. 1–3 mg) was added. After shaking the mixture for 24 h at r.t., the title compound, MS: m/e=316.2 (M+H+), was obtained from the reaction mixture by HPLC chromatography (YMC CombiPrep C18 column 50×20 mm, solvent gradient 10–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Sources & evidence

ORD record
ord-74da07a0b0e14852b581171b1b739882
Source dataset
uspto-grants-2006_11
Patent number
US07138404B2

Reaction notes

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