2-Methoxyethyl chloroformate → HCID 59244664, compound

HRID 912180Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=CC=1.Cl[C:42]([O:44][CH2:45][CH2:46][O:47][CH3:48])=[O:43]>>[CH3:48][O:47][CH2:46][CH2:45][O:44][C:42]([N:27]1[C:17]2[N:18]=[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:20]=[C:15]([C:12]3[CH:11]=[N:10][C:9]([NH2:8])=[N:14][CH:13]=3)[C:16]=2[CH2:29][CH2:28]1)=[O:43]

Participants

Reactant 2

HCID 694002-Methoxyethyl chloroformate

HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Product 1

HCID 59244664HCID 59244664, compoundYield 72%

Procedure

In the same manner as Example 1-D-01, using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (40 mg) and 2-methoxy-ethyl chloroformate (0.021 ml) instead of acetic anhydride, a colorless oily crude product (60 mg) of 4-(2-bis-(4-methoxy-benzyl)-amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid 2-methoxy-ethyl ester was obtained. The obtained colorless oily crude product (60 mg) of 4-(2-bis-(4-methoxy-benzyl)-amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid 2-methoxy-ethyl ester was subjected to deprotection reaction according to the above deprotection reaction method 2, to obtain 4-(2-amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid 2-methoxy-ethyl ester as a colorless solid (21 mg, 72%).

Workup

customaccording to the above deprotection reaction method 2

Sources & evidence

ORD record: ord-927360ba418f4493b987d1d254a8c4be
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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