HCID 59333753, compound → HCID 59333710, compound

HRID 1930703Notes

Reaction equation

HRID 1930703 reaction equation
C[Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:20]=[C:21](C(OCC)=O)[C:22]3[CH2:28][O:27][CH2:26][CH2:25][C:23]=3[N:24]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1>C1COCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:20]=[C:21]([C:6]([OH:5])([CH3:7])[CH3:11])[C:22]3[CH2:28][O:27][CH2:26][CH2:25][C:23]=3[N:24]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 59333753HCID 59333753, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 59333710HCID 59333710, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (0.769 mL, 0.77 mmol) was added at 0° C. to a solution of ethyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-4-carboxylate (150 mg, 0.37 mmol) in dry THF (5 mL). 4 eq extra equivalents of methylmagnesium bromide were added over 2 h. The crude product was partitioned between DCM and water. The organic phase was separated and the solvent was evaporated. The crude product was purification on a prepHPLC affording 2-(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-yl)propan-2-ol (11.00 mg, 7.59%). MS (ES+) m/z 396.2 (M+H)+;

Workup

  1. customThe crude product was partitioned between DCM and water
  2. customThe organic phase was separated
  3. customthe solvent was evaporated
  4. custompurification on

Sources & evidence

ORD record
ord-b39f91749e0349c8983aaaad8b489df9
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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