Ethyl Acetate → HCID 86759319, compound

HRID 1838970Notes

Reaction equation

HRID 1838970 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=O)=[C:4]([N:11]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:3]=1.[CH2:30]([Mg]Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[NH4+].C(OCC)(=[O:43])C>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][CH2:30][C:31]2([OH:43])[CH:36]=[CH:35][CH:34]=[CH:33][CH2:32]2)=[C:4]([N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 54129137HCID 54129137, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 86759319HCID 86759319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-chloro-6-di(4-methoxybenzyl)amino-5-pyrimidine carbaldehyde (0.20 g; 0.48 mmol) was stirred in dry THF (5 ml) at 0 DC. Benzyl magnesium chloride (1.0 M; 3 eq; 1.45 mmol; 1.45 ml) was added dropwise. The mixture was stirred for, 30 mins before addition of saturated ammonium chloride solution (50 ml) and ethyl acetate (50 ml). The aqueous layer was further extracted with ethyl acetate and the organic layers combined, washed with water, dried and evaporated. The product was purified by column chromatography eluting with 40% EtOAc/petrol (40:60) giving a yellow oil (0.151 g; 0.30 mmol; 62.4%).

Workup

  1. extractionThe aqueous layer was further extracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe product was purified by column chromatography
  6. washeluting with 40% EtOAc/petrol (40:60)
  7. customgiving a yellow oil (0.151 g; 0.30 mmol; 62.4%)

Sources & evidence

ORD record
ord-673fb59e290f45538ec4ac504134da4f
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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