2-Amino-6-(3-hydroxyprop-1-ynyl)-4-(1,3-dihydroisoindol-2-yl-carbonyl)quinazoline → [2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]propynal

HRID 1887227Notes

Reaction equation

HRID 1887227 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[C:24][CH2:25][OH:26])[CH:8]=2)[N:3]=1>O1CCCC1.[O-2].[Mn+4].[O-2]>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[C:24][CH:25]=[O:26])[CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 594834682-Amino-6-(3-hydroxyprop-1-ynyl)-4-(1,3-dihydroisoindol-2-yl-carbonyl)quinazoline

Product 1

HCID 59483542[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]propynal

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

860 mg of 2-amino-6-(3-hydroxyprop-1-ynyl)-4-(1,3-dihydroisoindol-2-yl-carbonyl)quinazoline are dissolved in 2 ml of tetrahydrofuran and, after addition of 1.736 g of manganese(IV) oxide, stirred at room temperature for 16 h. After addition of a further 434 mg of manganese(IV) oxide, the mixture is stirred for a further 12 h, filtered through kieselguhr, and the filtrate is evaporated to dryness. Drying in vacuo gives 402 mg of “A965”.

Workup

  1. stirringthe mixture is stirred for a further 12 h
  2. filtrationfiltered through kieselguhr
  3. customthe filtrate is evaporated to dryness
  4. customDrying in vacuo
  5. customgives 402 mg of “A965”

Sources & evidence

ORD record
ord-55c6aca7ed17450786e05d5d6c5186bd
Source dataset
uspto-grants-2013_08
Patent number
US08501754B2

Reaction notes

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