Реакция #1126001

Уравнение реакции

6-(4-(4-amino-3-(tert-butyldimethylsilyloxy)azepan-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Boc2O

2,4-dichlorofuro[3,2-d]pyrimidine

6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

TBAF

→

6-(4-(4-amino-3-hydroxyazepan-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Выход 35.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   КонцентрированиеThe mixture was concentrated
3. 3
   Другоеpurified by preparatory HPLC (Table 2, Method t)

Методика

A mixture of 6-(4-(4-amino-3-(tert-butyldimethylsilyloxy)azepan-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.400 g, 0.724 mmol, prepared using F from Preparation #AH.1, O with Boc2O, K, A with 2,4-dichlorofuro[3,2-d]pyrimidine [Arkpharm], B with 6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one [ArkPharm] and C) and TBAF (0.378 g, 1.45 mmol) in THF (10 mL) was stirred at about 25° C. for about 4 h. The mixture was concentrated and purified by preparatory HPLC (Table 2, Method t) to give 6-(4-(4-amino-3-hydroxyazepan-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.11 g, 35%): LC/MS (Table 2, Method h) Rt=1.69 min.; MS m/z: 439 (M+H)+. Syk IC50=B

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