tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate → 4-Chloro-7-methoxy-6-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]methoxy}quinazoline

HRID 1948939Notes

Reaction equation

HRID 1948939 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([CH2:27]O)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([O:12][CH2:27][CH:24]3[CH2:25][CH2:26][N:22]([C:20]([O:19][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:21])[CH2:23]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 231324754-Chloro-7-methoxyquinazolin-6-ol

Product 1

HCID 866008284-Chloro-7-methoxy-6-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]methoxy}quinazolineYield 114.6%

Procedure

4-Chloro-7-methoxy-6-hydroxyquinazoline (2.5 g) was reacted with 1-(tert-butoxycarbonyl)-3-(hydroxymethyl)pyrrolidine (3.58 g) to give 4-chloro-7-methoxy-6-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]methoxy}quinazoline (5.36 g, 100%); 1H NMR Spectrum: (DMSO d6) 1.39 (s, 9H); 1.45-1.79 (m, 2H); 1.97-2.08 (m, 1H); 2.65-2.74 (m, 1H); 2.91-3.17 (m, 2H); 3.40-3.52 (m, 1H); 4.01 (s, 3H); 4.15-4.22 (m, 2H); 7.42 (s, 1H); 7.45 (s, 1H); 8.86 (s, 1H); Mass Spectrum: (M+H)+ 394.

Sources & evidence

ORD record
ord-84c8040d3ab2465f8161be992cf1d960
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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