Triphenylphosphine → HCID 86624372, compound

HRID 1948953Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:25][CH3:26])=[C:21]([OH:24])[CH:22]=2)[N:17]=[CH:16][N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH:55](O)[CH2:54]1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>ClCCl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:25][CH3:26])=[C:21]([O:24][CH:57]3[CH2:56][CH2:55][CH2:54][N:53]([C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:52])[CH2:58]3)[CH:22]=2)[N:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Diethyl azodicarboxylate (9.41 ml, 40% solution in toluene) was added to a mixture of 4-chloro-6-hydroxy-7-methoxyquinazoline (2.90 g; prepared as described in Example 16-preparation of starting materials), triphenylphosphine (5.43 g) and tert-butoxycarbonyl-3-hydroxypiperidine (4.15 g) in dichloromethane (75 ml). The resulting solution was heated to 40° C. for 6 hours, and then allowed to stand overnight at room temperature. This was purified by flash column chromatography eluting with isohexane (79%), acetone (20%), and triethylamine (1%) to give 4-chloro-7-methoxy-6-[1-(tert-butoxycarbonyl)piperidin-3-yloxy]quinazoline as a white solid (2.47 g, 53%); 1H NMR Spectrum: (CDCl3) 1.5 (m, 9H); 1.6 (m, 1H); 1.9 (m, 2H); 2.1 (m, 1H); 3.5 (m, 1H); 3.6 (m, 1H); 4.0 (s, 3H); 4.2-3.9 (m, 2H); 4.5 (m, 1H); 7.3 (s, 1H); 7.4 (s, 1H); 8.9 (s, 1H); Mass Spectrum: (M+H): 394.

Workup

customThis was purified by flash column chromatography
washeluting with isohexane (79%), acetone (20%), and triethylamine (1%)

Sources & evidence

ORD record: ord-645a2776754c4d83a3e8df11e14b5634
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399667B2

Reaction notes

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