4,6-Dichloropyrimidine → 6-chloro-N-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]pyrimidin-4-amine

HRID 447589Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][C@H:13]3[CH2:15][C@H:16]([NH2:18])[CH2:17][C@H:12]3[CH2:11][O:10]2)=[CH:5][CH:4]=1.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CCO>[Cl:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([NH:18][C@H:16]2[CH2:15][C@@H:13]3[O:14][CH:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[O:10][CH2:11][C@@H:12]3[CH2:17]2)[CH:25]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A sealed tube containing (4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-amine (120. mg, 0.481 mmol), 4,6-dichloropyrimidine (143 mg, 0.963 mmol), DIPEA (0.0920 mL, 0.528 mmol) and EtOH (30.0 mL) was heated to 110° C. for 20 h. The cooled mixture was concentrated in vacuo and the residue was purified via silica gel chromatography eluting with a gradient of 0 to 5% MeOH in DCM (120. mg, 69%). LC/MS: Rt=1.74 min, ES+ 362 (AA standard).

Workup

concentrationThe cooled mixture was concentrated in vacuo
customthe residue was purified via silica gel chromatography
washeluting with a gradient of 0 to 5% MeOH in DCM (120. mg, 69%)

Sources & evidence

ORD record: ord-122a5c6f7ae74c9199dc650d1659c679
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481550B2

Reaction notes

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