Acetic Acid → HCID 10268713, compound

HRID 722079Notes

Reaction equation

HRID 722079 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][S:6][C:7]1[N:12]=[C:11]([NH2:13])[C:10]([CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][N:8]=1)[CH3:2].[CH:21](=O)[CH3:22].C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.C(O)(C(F)(F)F)=O.CC#N>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][S:6][C:7]1[N:12]=[C:11]([NH:13][CH2:21][CH3:22])[C:10]([CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][N:8]=1)[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9922683HCID 9922683, compound

Product 1

HCID 10268713HCID 10268713, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (4-Amino-5-thiophen-2-ylmethyl-pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester (0.5 mmol, 155 mg) as prepared in example 12 and acetaldehyde (0.6 mmol, 27 mg) in 1.25 ml of DMF was added acetic acid (0.25 ml) and sodium cyanoborohydride (0.6 mmol, 38 mg) and the mixture was shaken for two days at r.t. The title compound, MS: m/e=338.2 (M+H+), was obtained from the 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-b886f83c41104441a1061e667a545a7e
Source dataset
uspto-grants-2006_11
Patent number
US07138404B2

Reaction notes

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