Ammonium formate → 1-[(S)-3-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-propan-1-one

HRID 242336Notes

Reaction equation

C([N:8]1[CH2:27][CH2:26][C:11]2[N:12]=[CH:13][N:14]=[C:15]([O:16][C@H:17]3[CH2:21][CH2:20][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:18]3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[N:12]1[C:11]2[CH2:26][CH2:27][NH:8][CH2:9][C:10]=2[C:15]([O:16][C@H:17]2[CH2:21][CH2:20][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:18]2)=[N:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Pd(OH)2 (150 mg, 1.070 mmol) was put into a round flask and flushed under argon for 5 minutes. A solution of 1-[(S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-propan-1-one (560 mg, 1.528 mmol) in 22 mL of MeOH was added followed by ammonium formate (482 mg, 7.64 mmol). The reaction mixture was stirred under reflux (70° C.) for 2 h. The mixture was filtered over a pad of celite and dried under high vacuum to give 1-[(S)-3-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-propan-1-one. No further purification (m=420 mg, quantitative yield). MS: [M+H]+=277.5 Rt(6)=0.71 min.

Workup

customflushed under argon for 5 minutes
filtrationThe mixture was filtered over a pad of celite
customdried under high vacuum

Sources & evidence

ORD record: ord-c888180205c846188ea927263ea08e15
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653092B2

Reaction notes

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